2-(Tributylstannyl)-1,3-thiazole → 2'-(2-(thiazol-2-yl)pyrimidin-4-yl)-5',6'-dihydrospiro[piperidine-4,7'-pyrrolo[3,2-c]pyridin]-4'(1'H)-one

HRID 513110Notes

Reaction equation

HRID 513110 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[NH:16][C:15]3[C:14]4([CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]4)[CH2:13][N:12](CC4C=CC(OC)=CC=4)[C:11](=[O:38])[C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:44]1[S:45][CH:46]=[CH:47][N:48]=1)CCC>>[S:45]1[CH:46]=[CH:47][N:48]=[C:44]1[C:2]1[N:7]=[C:6]([C:8]2[NH:16][C:15]3[C:14]4([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[CH2:13][NH:12][C:11](=[O:38])[C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 86671415HCID 86671415, compound

Product 1

HCID 683148622'-(2-(thiazol-2-yl)pyrimidin-4-yl)-5',6'-dihydrospiro[piperidine-4,7'-pyrrolo[3,2-c]pyridin]-4'(1'H)-one

Procedure

The title compound was prepared following the general procedure reported for Example 9—1 using A5 and 2-(tributylstannyl)thiazole, purified by semi-preparative HPLC (Method A) and was isolated as TFA-salt. 1H NMR (400 MHz, DMSO-D6, 300K): δ=1.90 (2H, d, J=14.1 Hz), 2.27 (2H, dt, J1=4.3 Hz, J2=14.4 Hz), 3.12 (2H, q, J=11.7 Hz), 3.30 (2H, s), 3.52 (2H, d, J=2.3), 7.36 (1H, d, J=1.9 Hz), 7.44 (1H, br s), 7.92 (1H, d, J=5.5 Hz), 8.01 (1H, d, J=3.1 Hz), 8.10 (1H, d, J=3.1 Hz), 8.26 (1H, br d, J=10.2 Hz), 8.78 (1H, br d, J=9.4 Hz), 8.83 (1H, d, J=5.5 Hz), 11.84 (1H, s); MS (ES) C18H18N6OS requires: 366. found: 367.1 [M+H]+.

Workup

  1. custompurified by semi-preparative HPLC (Method A)

Sources & evidence

ORD record
ord-dd8b8ce5944240bfa9605ac33de4fa91
Source dataset
uspto-grants-2015_08
Patent number
US09102676B2

Reaction notes

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