Ethanesulfonylchloride, 2-chloro- → N4-(2-((2-chloroethyl)sulfonyl)-2-azaspiro[3.3]heptan-6-yl)-5-(4-phenoxyphenyl)pyrimidine-4,6-diamine

HRID 1522204Notes

Reaction equation

HRID 1522204 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.C(OC([N:17]1[CH2:20][C:19]2([CH2:23][CH:22]([NH2:24])[CH2:21]2)[CH2:18]1)=O)(C)(C)C.[O:25]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl:41][CH2:42][CH2:43][S:44](Cl)(=[O:46])=[O:45]>>[Cl:41][CH2:42][CH2:43][S:44]([N:17]1[CH2:18][C:19]2([CH2:21][CH:22]([NH:24][C:7]3[C:2]([C:29]4[CH:30]=[CH:31][C:26]([O:25][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)=[CH:27][CH:28]=4)=[C:3]([NH2:9])[N:4]=[CH:5][N:6]=3)[CH2:23]2)[CH2:20]1)(=[O:46])=[O:45]

Participants

5

Reactant 4

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 46930560tert-Butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylate

Product 1

HCID 86721803N4-(2-((2-chloroethyl)sulfonyl)-2-azaspiro[3.3]heptan-6-yl)-5-(4-phenoxyphenyl)pyrimidine-4,6-diamineYield 11.2%

Procedure

N4-(2-((2-chloroethyl)sulfonyl)-2-azaspiro[3.3]heptan-6-yl)-5-(4-phenoxyphenyl)pyrimidine-4,6-diamine (10.5 mg, 11.2%) was prepared from 5,6-dichloropyrimidin-4-amine, 6-amino-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester, (4-phenoxyphenyl)boronic acid and 2-chloro-ethanesulfonyl chloride according to general scheme 3 using methods S1, S2, S3, and S4C. HPLC purity 95%. MS: m/z=501 [M+H]+. 1H NMR (CD3OD) δ 8.24 (s, 1H), 7.10-7.47 (m, 9H), 6.70 (m, 1H), 6.19 (d, 1H), 6.01 (d, 1H), 4.62 (m, 1H), 3.58 (s, 2H), 3.13 (s, 2H), 2.37 (m, 2H), 1.81 (m, 2H).

Sources & evidence

ORD record
ord-701a32c996ab4eacbc46c1322b37b149
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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