2,3,4,5-Tetrahydrobenzo[F][1,4]thiazepine 1,1-dioxide → HCID 71548636, compound

HRID 1910451Notes

Reaction equation

[NH2:1][C:2]1([CH2:6][NH:7][C:8]2[C:9]3[S:17][CH:16]=[CH:15][C:10]=3[N:11]=[C:12](Cl)[N:13]=2)[CH2:5][O:4][CH2:3]1.[NH2:18][CH2:19][C:20]1([NH:24][C:25]2[C:26]3[S:34][CH:33]=[CH:32][C:27]=3[N:28]=[C:29](Cl)[N:30]=2)[CH2:23][O:22][CH2:21]1.[CH:35]1[C:40]2[CH2:41][NH:42][CH2:43][CH2:44][S:45](=[O:47])(=[O:46])[C:39]=2[CH:38]=[CH:37][CH:36]=1>C(O)CCC>[NH2:1][C:2]1([CH2:6][NH:7][C:8]2[C:9]3[S:17][CH:16]=[CH:15][C:10]=3[N:11]=[C:12]([N:42]3[CH2:41][C:40]4[CH:35]=[CH:36][CH:37]=[CH:38][C:39]=4[S:45](=[O:47])(=[O:46])[CH2:44][CH2:43]3)[N:13]=2)[CH2:5][O:4][CH2:3]1.[NH2:18][CH2:19][C:20]1([NH:24][C:25]2[C:26]3[S:34][CH:33]=[CH:32][C:27]=3[N:28]=[C:29]([N:42]3[CH2:41][C:40]4[CH:35]=[CH:36][CH:37]=[CH:38][C:39]=4[S:45](=[O:47])(=[O:46])[CH2:44][CH2:43]3)[N:30]=2)[CH2:23][O:22][CH2:21]1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of N-[(3-aminooxetan-3-yl)methyl]-2-chlorothieno[3,2-d]pyrimidin-4-amine and N-[3-(aminomethyl)oxetan-3-yl]-2-chlorothieno[3,2-d]pyrimidin-4-amine (184 mg, 0.66 mmol), 6,7,8,9-tetrahydro-5-thia-8-aza-benzocycloheptene-5,5-dioxide (680 mg, 3.44 mmol) in n-Butanol (1 mL) was heated at 160° C. for 30 min. The crude was purified by preparative HPLC to afford N-[(3-aminooxetan-3-yl)methyl]-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)thieno[3,2-d]pyrimidin-4-amine and N-[3-(aminomethyl)oxetan-3-yl]-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)thieno[3,2-d]pyrimidin-4-amine.

Workup

customThe crude was purified by preparative HPLC

Sources & evidence

ORD record: ord-2307a7509920415eb715ecaf5c44e53f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604019B2

Reaction notes

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