Chloride → HCID 68008112, compound

HRID 526941Notes

Reaction equation

C(N[C:6]([N:8]1[CH2:13]CC[C@@H](CNC2C(F)=CN=C(C3C4C(=NC=C(Cl)C=4)NC=3)N=2)[CH2:9]1)=[O:7])(C)(C)C.[NH2:33][C@@H:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]1[CH2:40][NH:41][C:42]1[C:47]([F:48])=[CH:46][N:45]=[C:44]([C:49]2[C:57]3[C:52](=[N:53][CH:54]=[C:55]([Cl:58])[CH:56]=3)[N:51](S(C3C=CC(C)=CC=3)(=O)=O)[CH:50]=2)[N:43]=1.[Cl-]>>[Cl:58][C:55]1[CH:56]=[C:57]2[C:49]([C:44]3[N:43]=[C:42]([NH:41][CH2:40][C@@H:35]4[CH2:36][CH2:37][CH2:38][CH2:39][C@H:34]4[NH:33][C:6](=[O:7])[N:8]([CH3:13])[CH3:9])[C:47]([F:48])=[CH:46][N:45]=3)=[CH:50][NH:51][C:52]2=[N:53][CH:54]=1

Participants

Reactant 3

HCID 312Chloride

HCID 68007303HCID 68007303, compound

HCID 68007392N-((trans-2-aminocyclohexyl)methyl)-2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-amine

Product 1

HCID 68008112HCID 68008112, compound

Procedure

Urea 564 was prepared according to the procedure for compound 20 (Scheme 12A) using N-((trans-2-aminocyclohexyl)methyl)-2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-amine, 14f, and dimethylcarbomoyl chloride, afforded desired product, 564, as a racemic mixture of trans isomers.

Workup

customUrea 564 was prepared

Sources & evidence

ORD record: ord-9e6c1fe8da6b4ea0a2170dd1e0c72328
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345708B2

Reaction notes

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