Diisopropylethylamine → HCID 136216310, 화합물

HRID 1748774노트

반응식

HRID 1748774 반응식
[CH2:1]([N:3]1[C:7]2[NH:8][CH2:9][CH2:10][S:11][CH:12]([C:13]3[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][C:14]=3[CH3:22])[C:6]=2[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[N:4]1)[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:62][N:63]1[C:67]([NH2:68])=[CH:66][CH:65]=[N:64]1>CN(C=O)C>[CH2:1]([N:3]1[C:7]2[NH:8][CH2:9][CH2:10][S:11][CH:12]([C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH:68][C:67]4[N:63]([CH3:62])[N:64]=[CH:65][CH:66]=4)=[O:19])=[CH:15][C:14]=3[CH3:22])[C:6]=2[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[N:4]1)[CH3:2]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 136348443HCID 136348443, 화합물

생성물 1

HCID 136216310HCID 136216310, 화합물수율 42.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-(1-ethyl-3-(pyridin-2-yl)-4,6,7,8-tetrahydro-1H-pyrazolo[3,4-e][1,4]thiazepin-4-yl)-3-methylbenzoic acid (0.60 g, 1.521 mmol, Preparation # V.1) and DIEA (0.80 mL, 4.56 mmol), in DMF was added HATU (0.64 g, 1.67 mmol). The reaction mixture was stirred for about 30 min and 1-methyl-1H-pyrazol-5-amine (0.22 g, 2.28 mmol, Aldrich) was added. The reaction mixture stirred for about 5 h and was concentrated under reduced pressure. The residue was dissolved in DCM (15 mL) and washed with saturated NaHCO3 (5 mL). The organic layer was separated and dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by RP-HPLC (Table 2, Method e), to afford 4-(1-ethyl-3-(pyridin-2-yl)-4,6,7,8-tetrahydro-1H-pyrazolo[3,4-e][1,4]thiazepin-4-yl)-3-methyl-N-(1-methyl-1H-pyrazol-5-yl)benzamide (0.30 g, 0.64 mmol, 42%) as a white solid. LC-MS (Table 1, Method g) Rt=2.01 min, m/z 474 (M+H)+; 1H NMR (DMSO-d6) δ 10.11 (s, 1H), 8.52-8.48 (m, 1H), 7.87-7.81 (m, 1H), 7.76-7.70 (m, 2H), 7.62 (dd, J=8.1, 1.8 Hz, 1H), 7.36 (d, J=1.9 Hz, 1H), 7.33 (d, J=8.1 Hz, 1H), 7.24-7.18 (m, 1H), 6.89 (s, 1H), 6.19 (d, J=1.9 Hz, 1H), 5.83 (d, J=4.6 Hz, 1H), 4.31-4.00 (m, 2H), 3.76-3.68 (m, 1H), 3.65 (s, 3H), 3.06-2.95 (m, 1H), 2.77-2.62 (m, 2H), 2.60 (s, 3H), 1.34 (t, J=7.1 Hz, 3H).

후처리

  1. stirringThe reaction mixture stirred for about 5 h
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in DCM (15 mL)
  4. washwashed with saturated NaHCO3 (5 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by RP-HPLC (Table 2, Method e)

출처 및 근거

ORD 기록
ord-282df817a46b4aed86435fb0e6d7c89a
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150592B2

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