Ammonia → HCID 86678986, compound

HRID 2203353Notes

Reaction equation

HRID 2203353 reaction equation
[NH3:1].CO.[NH2:4][C:5]1[C:6]2[C:31]([CH3:37])([C:32]([O:34]CC)=O)[C:30](=[O:38])[NH:29][C:7]=2[N:8]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][CH2:21][C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])[N:12]=2)[N:10]=1>>[NH2:4][C:5]1[C:6]2[C:31]([CH3:37])([C:32]([NH2:1])=[O:34])[C:30](=[O:38])[NH:29][C:7]=2[N:8]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][CH2:21][C:22]([F:27])([F:28])[C:23]([F:26])([F:25])[F:24])[N:12]=2)[N:10]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86678987HCID 86678987, compound

Product 1

HCID 86678986HCID 86678986, compound

Procedure

A 2 M solution of ammonia in MeOH (28.6 mL, 57.3 mmol) was added to ethyl 4-amino-5-methyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, as prepared by the procedure described in Example 158, (220 mg, 0.441 mmol) and the resultant mixture heated at 50° C. for 16 hours. The reaction mixture was concentrated in vacuo and the residue purified by silica gel column chromatography using a DCM/MeOH (with 0.5% NH4OH) gradient. Chiral separation by SFC using a Chiralpak AD column provided both enantiomers of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 11.27 (1H, s), 9.02 (1H, dd, J=8.06, 1.62 Hz), 8.64 (1H, dd, J=4.50, 1.63 Hz), 7.45 (1H, s), 7.38 (1H, dd, J=8.07, 4.49 Hz), 7.19 (1H, s), 6.82 (2H, s), 4.88 (2H, t, J=6.80 Hz), 3.04-2.90 (2H, m), 1.57 (3H, s). m/z=471.1 (M+H).

Workup

  1. customas prepared by the procedure
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue purified by silica gel column chromatography
  4. customChiral separation by SFC

Sources & evidence

ORD record
ord-f78afe2ed16b4ce7b9964389c4957dc5
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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