Dimethylformamide → HCID 86662346, compound

HRID 1397918Notes

Reaction equation

HRID 1397918 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)C(O)=O)(=[O:13])=[O:12])[CH2:6][CH2:5]2.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[N:30]=[C:31]([NH2:34])[S:32][CH:33]=1.CN([CH:38]=[O:39])C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:22]=[CH:21][C:20]([C:38]([NH:34][C:31]3[S:32][CH:33]=[C:29]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=4)[N:30]=3)=[O:39])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH2:6][CH2:5]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10924594-(Pyridin-2-yl)-1,3-thiazol-2-amineHCID 66763110HCID 66763110, compound

Product 1

HCID 86662346HCID 86662346, compound

Procedure

3-(5-chloroindolin-1-ylsulfonyl)benzoic acid (8) (100 mg, 0.30 mmol) was treated with 4-(pyridin-2-yl)thiazol-2-amine (44 mg, 0.25 mmol) in DMF (2 mL) using method C. The residue was purified using flash chromatography eluting with EtOAc. The resulting solid was triturated with diethyl ether to give 4-(5-chloroindolin-1-ylsulfonyl)-N-(4-(pyridin-2-yl)thiazol-2-yl)benzamide as an off white solid. Yield: 53 mg (43%). 1H-NMR: 8.63-8.59 (m, 1H), 8.25 (d, J=8.5 Hz, 2H), 8.02-7.86 (m, 5H), 7.49 (d, J=8.5 Hz, 1H), 7.34 (ddd, J=7.5, 5.0, 1.0 Hz, 1H), 7.29-7.24 (m, 2H), 4.00 (t, J=8.5 Hz, 2H), 2.94 (t, J=8.5 Hz, 2H)

Workup

  1. customThe residue was purified
  2. washeluting with EtOAc
  3. customThe resulting solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-ede2dff1b9ae42d88be0f4be4952131c
Source dataset
uspto-grants-2014_12
Patent number
US08901306B2

Reaction notes

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