Dimethyl Sulfoxide → HCID 178516971, compound

HRID 707448Notes

Reaction equation

Cl.[NH2:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3=[N:12][CH:13]=[C:14]([Br:16])[N:15]=[C:10]3[N:9]([CH:17]3[CH2:19][CH2:18]3)[C:8]2=[O:20])[CH2:4]1.CS(C)=O.C(N(CC)C(C)C)(C)C.Cl[C:35]1[S:36][C:37]2[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=2[N:39]=1>O.CO>[S:36]1[C:37]2[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=2[N:39]=[C:35]1[NH:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3=[N:12][CH:13]=[C:14]([Br:16])[N:15]=[C:10]3[N:9]([CH:17]3[CH2:18][CH2:19]3)[C:8]2=[O:20])[CH2:4]1

Participants

Conditions

Temperature: 100 °C

Procedure

A glass microwave reaction vessel was charged with 1-(trans-3-aminocyclobutyl)-5-bromo-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride (Intermediate 82, 0.128 g, 0.355 mmol) and DMSO (2 mL). N,N-Diisopropylethylamine (0.250 ml, 1.437 mmol) was added followed by 2-chlorobenzothiazole (0.060 ml, 0.461 mmol) and the reaction mixture was sealed under argon and heated at 100° C. for 24 h. The reaction mixture was diluted with water and a small amount of MeOH. The resultant solid was filtered, washed with water and dried in vacuo to give 94 mg (58%) of an off-white crystalline solid. ESI MS 456.8, 458.8 [M+1]. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.53 (d, J=6.28 Hz, 1 H), 8.16 (s, 1 H), 7.63-7.75 (m, 1 H), 7.42 (d, J=7.45 Hz, 1 H), 7.15-7.30 (m, 1 H), 6.96-7.09 (m, 1 H), 5.12 (quin, J=8.29 Hz, 1 H), 4.41-4.65 (m, 1 H), 3.14-3.29 (m, 2 H), 2.87-3.01 (m, 1 H), 2.39-2.57 (m, 2 H), 0.91-1.11 (m, 4 H)

Workup

customA glass microwave reaction vessel
customthe reaction mixture was sealed under argon
filtrationThe resultant solid was filtered
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-4672a7318b9946388b8cd223d277aaf8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174992B2

Reaction notes

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