N-methyl-2-pyrrolidone → HCID 24986285, compound

HRID 2251096Notes

Reaction equation

HRID 2251096 reaction equation
[C:1]1([S:7]([C:10]2[N:22]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:13]3[N:14]=[C:15](S(C)(=O)=O)[N:16]=[CH:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:30](N(C(C)C)CC)(C)[CH3:31].Cl.[NH2:40][CH:41](C)[C:42](C)([OH:44])C.C[N:48]1CCCC1=O>>[C:1]1([S:7]([C:10]2[N:22]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:13]3[N:14]=[C:15]([NH:48][N:40]4[CH2:31][CH2:30][O:44][CH2:42][CH2:41]4)[N:16]=[CH:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 23434633HCID 23434633, compoundHCID 69216638HCID 69216638, compound

Product 1

HCID 24986285HCID 24986285, compound

Conditions

Temperature
90 °C

Procedure

6-Benzenesulfonyl-7-(4-fluoro-phenyl)-2-methanesulfonyl-7H-pyrrolo[2,3-d]pyrimidine, 34, (0.04 g, 0.10 mmol) in N-methylpyrrolidinone (3 mL) is added diisopropylethylamine (0.41 mL, 2.36 mmol) and 3-amino-2-methyl-butan-2-ol hydrochloride salt (0.10 g, 0.71 mmol). The mixture is heated to 90° C. for 21 hours. The product is purified by preparative HPLC to afford 50 mg of the desired product as a yellowish solid: 1H NMR (300 MHz, d6-DMSO) δ 8.64 (s, 1H), 7.64-7.47 (m, 1H), 7.42-7.25 (m, 5H), 7.14-7.09 (m, 1H), 6.56 (s, 1H), 5.95 (s, 1H), 4.30 (s, 1H), 3.85 (q, J=7.2 Hz, 2H), 1.04 (s, 9H), 0.93 (t, J=7.2 Hz, 3H); ESI+ MS: m/z (rel intensity) 540.9 (100, M++H).

Workup

  1. customThe product is purified by preparative HPLC

Sources & evidence

ORD record
ord-a2dc9f11e71c4af898d7e2e525c1aadf
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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