HCID 58529582, compound → HCID 58529856, compound

HRID 1972983Notes

Reaction equation

[NH2:1][C:2]1[C:7]2=[C:8](Br)[CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.[CH2:25]([C:32]1[S:33][C:34]2[CH:40]=[C:39](B3OC(C)(C)C(C)(C)O3)[CH:38]=[CH:37][C:35]=2[N:36]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[NH2:1][C:2]1[C:7]2=[C:8]([C:39]3[CH:38]=[CH:37][C:35]4[N:36]=[C:32]([CH2:25][C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)[S:33][C:34]=4[CH:40]=3)[CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

Reactant 2

HCID 58529582HCID 58529582, compound

HCID 59231971HCID 59231971, compound

Product 1

HCID 58529856HCID 58529856, compoundYield 87%

Procedure

In a manner similar to the procedure described for step 7 of the preparation of Example 330 and using tert-butyl 4-(4-amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)piperidine-1-carboxylate and 2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazole as starting material, 510 mg (87%) of the desired product was isolated. 1H NMR (400 MHz, DMSO-d6) δ 7.99 (s, 1H), 7.97 (d, 1H), 7.81 (s, 1H), 7.51 (d, 1H), 7.38-7.32 (m, 5H), 7.56 (s, 1H), 4.41 (s, 2H), 4.12-4.04 (m, 2H), 3.81 (s, 2H), 3.32-3.28 (m, 1H), 2.88-2.82 (m, 2H), 2.01-1.96 (m, 2H), 1.60-1.52 (m, 2H), 1.38 (s, 9H); LC-MS m/z [M+H]+ 541.1, RT 3.40 min.

Workup

customIn a manner similar to the procedure described for step 7 of the preparation of Example 330

Sources & evidence

ORD record: ord-04dbd7e5dc68496398249fd182c56436
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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