HCID 58529647, compound → HCID 58529454, compound

HRID 1972987Notes

Reaction equation

[CH2:1]([C:8]1[S:9][C:10]2[CH:16]=[CH:15][C:14](B3OC(C)(C)C(C)(C)O3)=[CH:13][C:11]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:26][C:27]1[C:32]2=[C:33](Br)[CH:34]=[C:35]([CH:36]3[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH2:37]3)[N:31]2[N:30]=[CH:29][N:28]=1>>[NH2:26][C:27]1[C:32]2=[C:33]([C:14]3[CH:15]=[CH:16][C:10]4[S:9][C:8]([CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[N:12][C:11]=4[CH:13]=3)[CH:34]=[C:35]([CH:36]3[CH2:37][CH2:38][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:40][CH2:41]3)[N:31]2[N:30]=[CH:29][N:28]=1

Participants

Reactant 2

HCID 58529647HCID 58529647, compound

HCID 59231971HCID 59231971, compound

Product 1

HCID 58529454HCID 58529454, compoundYield 95.6%

Procedure

In a manner similar to the procedure described for step 7 of the preparation of Example 330 and using 2-benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazole and tert-butyl 4-(4-amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)piperidine-1-carboxylate as starting material, 411 mg (95.6%) of the desired product was isolated. 1H NMR (400 MHz, CD2Cl2) δ 8.06 (s, 1H), 8.94 (s, 1H), 8.92 (d, 1 H), 7.49 (d, 1H), 7.37-7.45 (m, 5 H), 6.59 (s, 1H), 4.49 (s, 2 H), 4.25 (m, 2 H), 3.42 (m, 1H), 2.94 (m, 2H), 2.11 (m, 2H), 1.76-1.64 (m, 2 H), 1.48 (s, 9H); LC-MS m/z [M+H]+541.2, RT 3.37 min.

Workup

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

Sources & evidence

ORD record: ord-616f4d84d62e4841b056cf51fc9e6acb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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