Dimethylformamide → 2-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-1-morpholin-4-ylethanone

HRID 1926349Notes

Reaction equation

HRID 1926349 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][C:14]([OH:16])=O)[CH:12]=2)=[CH:4][C:3]=1[C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C=O)C>CCOC(C)=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][C:14]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:16])[CH:12]=2)=[CH:4][C:3]=1[C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67521113[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-acetic acid

Product 1

HCID 675205632-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-1-morpholin-4-ylethanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [4-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-acetic acid (5.00 mg, 0.0142 mmol), morpholine (10.0 mg, 0.11 mmol), TBTU (9.14 mg, 0.0284 mmol), DIPEA (0.02 mL, 0.1 mmol) and DMF (2 mL, 0.03 mol) was stirred at rt for 10 min. The solution was transferred to a separatory funnel, diluted with EtOAc and washed 3× with water. The organic layer was concentrated in vacuo and loaded onto a prep TLC plate, eluting with 5% MeOH/DCM. The band containing the pure product was filtered off using 1:1 MeOH/DCM, and the filtrate was concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=3.60-3.64 (m, 4H), 3.72 (dt, J=12.8, 4.7 Hz, 4H), 5.17 (s, 2H), 7.40-7.45 (m, 1H), 7.48-7.54 (m, 1H), 7.85 (s, 1H), 7.94-7.98 (m, 2H), 8.02 (d, J=7.8 Hz, 1H), 8.16 (d, J=2.3 Hz, 1H), 8.30 (d, J=2.3 Hz, 1H). MS (ES+): m/z=421.12 (100) [MH+]. HPLC: tR=2.79 min (ZQ3, polar—5 min).

Workup

  1. customThe solution was transferred to a separatory funnel
  2. washwashed 3× with water
  3. concentrationThe organic layer was concentrated in vacuo
  4. washeluting with 5% MeOH/DCM
  5. additionThe band containing the pure product
  6. filtrationwas filtered off
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a7af859888a8443588189c14137ffd02
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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