HCID 78322881, compound → HCID 86711301, compound

HRID 336170Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[N:13][C:14]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:9](Br)[N:8]([CH2:22][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=[CH2:25])[C:4]=2[N:5]=[CH:6][N:7]=1.NC1C2C(C3C=NC4C(C=3)=CC=CC=4)=C3N(C=2N=CN=1)C[C@@H](NC(=O)OC(C)(C)C)CC3>>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[N:13][C:14]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:9]3[N:8]([C:4]=2[N:5]=[CH:6][N:7]=1)[CH2:22][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:24][CH2:25]3

Participants

Reactant 2

HCID 78322881HCID 78322881, compound

HCID 86711302HCID 86711302, compound

Product 1

HCID 86711301HCID 86711301, compoundYield 84.1%

Procedure

In accordance with Example 10, except that the (R)-tert-butyl (1-(4-amino-6-bromo-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)but-3-en-2-yl)carbamate (6.70 g) obtained in Reference Example 2 was used in place of the (S)-tert-butyl (1-(4-amino-6-bromo-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)but-3-en-2-yl)carbamate obtained in Example 10, (R)-tert-butyl (4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl)carbamate (4.76 g) (yield: 84%) was obtained as a light-yellow solid.

Sources & evidence

ORD record: ord-0218321c479b4d158bc8bbe4d8390dc9
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889666B2

Reaction notes

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