Sulfamide → HCID 178527252, compound

HRID 715608Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[N:15]3[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:5][CH2:4]1.[S:34](N)([NH2:37])(=[O:36])=[O:35]>O1CCOCC1>[Cl:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:14]1[N:15]([C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[C:16]2[C:12]([N:13]=1)=[C:11]([NH:10][CH2:9][CH:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][NH:37][SH:34](=[O:36])=[O:35])[CH2:4][CH2:5]1)[N:19]=[CH:18][N:17]=2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N-{[4-(aminomethyl)cyclohexyl]methyl}-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-amine (6.6 mg, 0.014 mmol, 1 eq.) in 5 mL of dioxane was added 10 mg of sulfamide. The reaction was heated to 80° C. and stirred 16 h. The reaction was concentrated in vacuo. The crude material was purified by silica gel column chromatography using 0-100% ethyl acetate/hexanes to yield 1.9 mg (25%) of N-{[4-({[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]amino}methyl)cyclohexyl]methyl}aminosulfonamide. 1H NMR (300 MHz, METHANOL-d4) δ ppm 0.80-1.17 (m, 2 H) 1.21-1.79 (m, 6 H) 1.93 (br. s., 2 H) 3.00 (d, J=7.16 Hz, 2 H) 3.59 (br. s., 2 H) 7.19-7.69 (m, 8 H) 8.13-8.35 (m, 1 H), [M+H]+ 562.2.

Workup

concentrationThe reaction was concentrated in vacuo
customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-9f9937de5e7447169e58939489cb863a
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187480B2

Reaction notes

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