2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine → HCID 86762626, compound

HRID 2409070Notes

Reaction equation

HRID 2409070 reaction equation
[NH2:1][CH:2]([C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][N:10](C(OC(C)(C)C)=O)[C:7]2=[CH:8][N:9]=1)[CH3:3].Cl[C:21]1[N:26]=[C:25]([NH:27][C:28]2[CH:32]=[C:31]([C@H:33]3[CH2:35][C@H:34]3[F:36])[NH:30][N:29]=2)[CH:24]=[CH:23][N:22]=1.ClC1N=C(NC2C=C(C3CC3)NN=2)C=CN=1>>[NH:10]1[C:7]2[C:8](=[N:9][C:4]([C@@H:2]([NH:1][C:21]3[N:26]=[C:25]([NH:27][C:28]4[CH:32]=[C:31]([C@H:33]5[CH2:35][C@H:34]5[F:36])[NH:30][N:29]=4)[CH:24]=[CH:23][N:22]=3)[CH3:3])=[CH:5][CH:6]=2)[CH:12]=[CH:11]1

Participants

4

Reactant 3

HCID 581691182-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amineHCID 86689839HCID 86689839, compoundHCID 86762627HCID 86762627, compound

Product 1

HCID 86762626HCID 86762626, compound

Procedure

The title compound was prepared following the procedure according to Example 9, using (S)-1-(1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine hydrochloride (referential example 17) and 2-chloro-N-(5-((1R,2R)-2-fluorocyclopropyl)-1H-pyrazol-3-yl)pyrimidin-4-amine (referential example 4) in place of (1H-pyrrolo[3,2-b]pyridin-5-yl)methanamine and 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (referential example 1), respectively, as starting materials. 1H NMR (400 MHz, DMSO-d6) δ 11.98 (br s, 1H), 11.18 (s, 1H), 9.33 (br s, 1H), 7.79 (d, J=5.6 Hz, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.57 (s, 1H), 7.16 (d, J=8.3 Hz, 1H), 6.93 (br s, 1H), 6.53 (s, 1H), 6.40 (br s, 1H), 6.10 (br s, 1H), 5.21 (s, 1H), 4.90 (d, J=65.8 Hz, 1H), 2.10-1.99 (m, 1H), 1.49 (d, J=6.9 Hz, 3H), 1.33 (s, 1H), 1.24 (s, 1H); MS (ESI) m/k: 379.2 [M+1]+.

Sources & evidence

ORD record
ord-068bdf8db9cc47d8a6b3e1a5e16daf00
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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