Dimethylformamide → HCID 86662346, compound

HRID 1482813Notes

Reaction equation

HRID 1482813 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-f36a29e9bd474d51b2e50cc88b589af1
Source dataset
uspto-grants-2016_08
Patent number
US09416101B2

Reaction notes

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