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Dimethylamine, hydrochloride → (2S,4S)-4-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-pyrrolidine-2-carboxylic acid dimethylamide

HRID 1926357
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HRID 1926357 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([C@@H:13]3[CH2:17][NH:16][C@H:15]([C:18]([OH:20])=O)[CH2:14]3)[CH:12]=2)=[CH:4][C:3]=1[C:21]1[S:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1.Cl.[CH3:31][NH:32][CH3:33].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:31][N:32]([CH3:33])[C:18]([C@@H:15]1[CH2:14][C@H:13]([N:11]2[CH:12]=[C:8]([C:5]3[CH:6]=[N:7][C:2]([NH2:1])=[C:3]([C:21]4[S:22][C:23]5[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=5[N:25]=4)[CH:4]=3)[CH:9]=[N:10]2)[CH2:17][NH:16]1)=[O:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 44160252(2S,4S)-4-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-pyrrolidine-2-carboxylic acid

생성물 1

HCID 44160253(2S,4S)-4-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-pyrrolidine-2-carboxylic acid dimethylamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (2S,4S)-4-[4-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-pyrrolidine-2-carboxylic acid (5.00 mg, 0.00969 mmol) in DMF (2 mL) at rt were added dimethylamine hydrochloride (20 mg, 0.25 mmol) and DIPEA (0.1 mL, 0.6 mmol), and the mixture was stirred for 1 min. TBTU (6.22 mg, 0.0194 mmol) was then added, and the solution was stirred for 10 min. The material was transferred to a separatory funnel. The organic layer was washed with water, and concentrated in vacuo. The material was loaded onto a prep TLC plate, eluting with 6% (7N NH3 in MeOH)/DCM. The band containing the product was collected and filtered off with 1:1 MeOH/DCM. The filtrate was concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=2.15-2.21 (m, 1H), 2.82-2.91 (m, 1H), 3.00 (s, 3H), 3.12 (s, 3H), 3.23 (dd, J=12.4, 6.3 Hz, 1H), 3.49 (dd, J=12.0, 3.4 Hz, 1H), 4.15 (t, J=8.3 Hz, 1H), 4.98-5.05 (m, 1H), 7.42-7.47 (m, 1H), 7.53 (td, J=7.7, 1.3 Hz, 1H), 7.85 (s, 1H), 8.02 (dd, J=11.6, 7.8 Hz, 2H), 8.13 (s, 1H), 8.20 (d, J=2.3 Hz, 1H), 8.32 (d, J=2.0 Hz, 1H). MS (ES+): m/z=434.14 (100) [MH+]. HPLC: tR=2.12 min (ZQ2, polar—5 min).

후처리

  1. stirringthe solution was stirred for 10 min
  2. customThe material was transferred to a separatory funnel
  3. washThe organic layer was washed with water
  4. concentrationconcentrated in vacuo
  5. washeluting with 6% (7N NH3 in MeOH)/DCM
  6. additionThe band containing the product
  7. customwas collected
  8. filtrationfiltered off with 1:1 MeOH/DCM
  9. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-7af8535b6aca4178933143e77d2c3c67
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178668B2

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