Dimethylformamide → 2-(1H-indazol-4-yl)-N-(methylsulfonyl)-4-morpholinothieno[3,2-d]pyrimidine-6-carboxamide

HRID 2262136Notes

Reaction equation

HRID 2262136 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([C:11]([OH:13])=O)=[CH:8][C:6]=2[N:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:32]1[CH2:42][CH2:41]N2[C:35](=[N:36]CCC2)[CH2:34][CH2:33]1.[CH3:43][S:44]([NH2:47])(=[O:46])=[O:45].C[N:49]([CH:51]=O)C>>[NH:49]1[C:51]2[C:34](=[C:33]([C:2]3[N:3]=[C:4]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[C:5]4[S:10][C:9]([C:11]([NH:47][S:44]([CH3:43])(=[O:46])=[O:45])=[O:13])=[CH:8][C:6]=4[N:7]=3)[CH:32]=[CH:42][CH:41]=2)[CH:35]=[N:36]1

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59593131HCID 59593131, compound

Product 1

HCID 595930342-(1H-indazol-4-yl)-N-(methylsulfonyl)-4-morpholinothieno[3,2-d]pyrimidine-6-carboxamide

Procedure

To 50 mg of 2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carboxylic acid in 1 mL of DMF was added 2 eq of carbonyldiimidazole. The reaction was stirred for 1 hour at room temperature before addition of a 1 mL solution containing 2.5 eq DBU and 2 eq of methanesulfonamide in DMF. The reaction was stirred overnight at ambient temperature and concentrated to dryness. The crude chloride was subjected to Procedure A to yield 13.8 mg of 206. MS (Q1) 459.1 (M)+.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-50a14bd775ab4d6290621ec25314ef45
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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