1,2-Dichloroethane → N-(5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-4-cyclopropylbenzamide

HRID 1924766Notes

Reaction equation

HRID 1924766 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[N:11]=[C:10]3[S:12][C:13]([NH2:15])=[N:14][C:9]3=[CH:8][CH:7]=2)[CH:3]=[N:2]1.[CH:16]1([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)[CH2:18][CH2:17]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C>[NH:1]1[CH:5]=[C:4]([C:6]2[N:11]=[C:10]3[S:12][C:13]([NH:15][C:23](=[O:24])[C:22]4[CH:26]=[CH:27][C:19]([CH:16]5[CH2:18][CH2:17]5)=[CH:20][CH:21]=4)=[N:14][C:9]3=[CH:8][CH:7]=2)[CH:3]=[N:2]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2820644-Cyclopropylbenzoic acidHCID 580153785-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine

Product 1

HCID 44547804N-(5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-4-cyclopropylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5B (25.0 mg, 1.0 equivalent) and 4-cyclopropylbenzoic acid (1.1 equivalent) were dissolved in DMF, followed by addition of HOBt (1.0 equivalent), EDC (1.0 equivalent), Et3N (2.0 equivalents). The mixture was stirred for 12 h at room temperature. The crude mixture was filtered and purified by LCMS to give the titled compound 5 as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.77-0.87 (m, 2H) 1.04-1.13 (m, 2H) 2.01-2.10 (m, 1H) 7.28 (d, J=8.34 Hz, 2H) 7.68 (t, J=7.58 Hz, 1H) 7.82-7.91 (m, 3H) 7.99 (d, J=8.34 Hz, 2H) 8.47 (s, 1H) 9.03 (s, 1H); ESI-MS: m/z 362.0 (M+H)+.

Workup

  1. filtrationThe crude mixture was filtered
  2. custompurified by LCMS

Sources & evidence

ORD record
ord-50bdde30342645e6a501c9c5b0b460da
Source dataset
uspto-grants-2012_05
Patent number
US08178555B2

Reaction notes

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