6-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylic acid → 6-[cyclohexyl(cyclopropylmethyl)amino]-N-(4-{[(2,3-dihydroxypropyl)amino]sulfonyl}phenyl)pyrimidine-4-carboxamide

HRID 1746729Notes

Reaction equation

HRID 1746729 reaction equation
[CH:1]1([N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:31][CH2:32][CH:33]([OH:36])[CH2:34][OH:35])(=[O:30])=[O:29])=[CH:24][CH:23]=1>>[CH:1]1([N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([S:28]([NH:31][CH2:32][CH:33]([OH:36])[CH2:34][OH:35])(=[O:30])=[O:29])=[CH:24][CH:23]=3)=[O:16])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 594468416-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylic acid2×HCID 594469564-amino-N-(2,3-dihydroxypropyl)benzenesulfonamide2×

Product 1

HCID 251827796-[cyclohexyl(cyclopropylmethyl)amino]-N-(4-{[(2,3-dihydroxypropyl)amino]sulfonyl}phenyl)pyrimidine-4-carboxamide

Procedure

Following the general method as outlined in Example 1, starting from 6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylic acid (Intermediate 13) and 4-amino-N-(2,3-dihydroxypropyl)benzenesulfonamide (Intermediate 15), the title compound was obtained as a brown solid after purification by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-c7e9c5614d5746e8b88535ba1a9184e5
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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