Trimethylsilyl isocyanate → 3-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)azetidine-1-carboxamide

HRID 526895Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH:18]4[CH2:21][N:20](S(CC5CCCC5)(=O)=O)[CH2:19]4)[C:14]([F:31])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.Cl.N1CC(NC2C(F)=CN=C(C3C4C(=NC=C(Cl)C=4)N(S(C4C=CC(C)=CC=4)(=O)=O)C=3)N=2)C1.[N:65]([Si](C)(C)C)=[C:66]=[O:67]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH:18]4[CH2:19][N:20]([C:66]([NH2:65])=[O:67])[CH2:21]4)[C:14]([F:31])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

Reactant 3

HCID 70696Trimethylsilyl isocyanate

HCID 67284924N-(azetidin-3-yl)-2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-amine hydrochloride

HCID 680079372-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-(cyclopentyl-methylsulfonyl)azetidin-3-yl)-5-fluoropyrimidin-4-amine

Product 1

HCID 672852603-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)azetidine-1-carboxamideYield 79%

Procedure

According to the procedure for compound 469 using 61 mg (0.11 mmol) of 6c and isocyanatotrimethylsilane (15.14 μL, 0.11 mmol) afforded 87 mg (79% yield) of 512, as a white solid:

Sources & evidence

ORD record: ord-c6c196ab0d274b5a993579a6d231d35f
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345708B2

Reaction notes

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