Ammonia → HCID 86678984, compound

HRID 2203352Notes

Reaction equation

HRID 2203352 reaction equation
[NH3:1].[NH2:2][C:3]1[C:4]2[C:30]([CH3:36])([C:31]([O:33]CC)=O)[C:29](=[O:37])[NH:28][C:5]=2[N:6]=[C:7]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH2:20][C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])[N:10]=2)[N:8]=1>>[NH2:2][C:3]1[C:4]2[C:30]([CH3:36])([C:31]([NH2:1])=[O:33])[C:29](=[O:37])[NH:28][C:5]=2[N:6]=[C:7]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH2:20][C:21]([F:27])([F:26])[C:22]([F:24])([F:23])[F:25])[N:10]=2)[N:8]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86678985HCID 86678985, compound

Product 1

HCID 86678984HCID 86678984, compound

Conditions

Temperature
50 °C

Procedure

Ammonia (2.0M in MeOH, 11 mL, 22 mmol) was added to ethyl 4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, as prepared by the procedure described in Example 157, (150 mg, 0.289 mmol, single enantiomer from SFC separation on Chiralpak AD column). The resultant mixture was heated at 50° C. for 16 hours. The reaction solution was then concentrated in vacuo, and the residue purified by preparative TLC using 5% MeOH in DCM (with 0.5% NH4OH) as the eluent to give the indicated compound. 1H NMR (500 MHz, DMSO-d6): δ 8.66 (d, J=8.7 Hz, 1H); 8.02 (d, J=1.4 Hz, 1H); 7.45 (br s, 1H); 7.27 (dd, J=8.7, 1.7 Hz, 1H); 7.19 (br s, 1H); 6.79 (br s, 2H); 4.82 (t, J=6.8 Hz, 2H); 2.95-2.85 (m, 2H); 1.56 (s, 3H). m/z=504.1 (M+H).

Workup

  1. customas prepared by the procedure
  2. customdescribed in Example 157, (150 mg, 0.289 mmol, single enantiomer from SFC separation on Chiralpak AD column)
  3. concentrationThe reaction solution was then concentrated in vacuo
  4. customthe residue purified by preparative TLC
  5. customto give the indicated compound

Sources & evidence

ORD record
ord-34e3a1bf7f814400a69bbcd77fd79351
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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