Dimethylformamide → 3-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-1-pyrrolidin-1-ylpropan-1-one

HRID 1926353Notes

Reaction equation

HRID 1926353 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][CH2:14][C:15](O)=[O:16])[CH:12]=2)=[CH:4][C:3]=1[C:18]1[S:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]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][CH2:14][C:15]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:16])[CH:12]=2)=[CH:4][C:3]=1[C:18]1[S:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 675206793-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-propionic acid

Product 1

HCID 675209683-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-1-pyrrolidin-1-ylpropan-1-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[4-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-propionic acid (7.0 mg, 0.013 mmol), pyrrolidine (9 mg, 0.1 mmol), TBTU (8.24 mg, 0.0257 mmol), DIPEA (0.02 mL, 0.1 mmol), and DMF (2 mL, 0.02 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=1.85 (q, J=6.4 Hz, 2H), 1.88-1.96 (m, 2H), 2.92 (t, J=6.6 Hz, 2H), 3.39 (q, J=7.1 Hz, 4H), 4.49 (t, J=6.6 Hz, 2H), 7.39-7.44 (m, 1H), 7.47-7.52 (m, 1H), 7.81 (s, 1H), 7.94-7.97 (m, 2H), 8.00 (d, J=7.8 Hz, 1H), 8.12 (d, J=2.3 Hz, 1H), 8.27 (d, J=2.3 Hz, 1H). MS (ES+): m/z=419.13 (100) [MH+]. HPLC: tR=2.99 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-5f5cbb5904dd4166a696faec3b761a4a
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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