Cyclopropylamine → HCID 86678990, compound

HRID 2203355Notes

Reaction equation

HRID 2203355 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[NH2:5][C:6]1[C:7]2[C:32]([CH3:38])([C:33](OCC)=[O:34])[C:31](=[O:39])[NH:30][C:8]=2[N:9]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[N:13]=2)[N:11]=1>>[NH2:5][C:6]1[C:7]2[C:32]([CH3:38])([C:33]([NH:4][CH:1]3[CH2:3][CH2:2]3)=[O:34])[C:31](=[O:39])[NH:30][C:8]=2[N:9]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:25])([F:27])[F:26])[N:13]=2)[N:11]=1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 86678987HCID 86678987, compound

Product 1

HCID 86678990HCID 86678990, compound

Procedure

Cyclopropylamine (10.71 mL, 155 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, (594 mg, 1.189 mmol) and the resultant mixture heated at 50° C. for 16 hours. The mixture was concentrated in vacuo and the residue purified by silica gel column chromatography using a hexanes/EtOAc gradient. Chiral separation using SFC on a Chiralpak AD-H column provided both enantiomers of the title compound, 1H NMR (500 MHz, DMSO-d6): δ 9.02 (1H, d, J=8.09 Hz), 8.63 (1H, d, J=4.45 Hz), 7.63 (1H, d, J=4.01 Hz), 7.38 (1H, dd, J=8.08, 4.48 Hz), 6.75 (2H, s), 4.87 (2H, t, J=6.77 Hz), 3.03-2.90 (2H, m), 2.68-2.62 (1H, m), 1.56 (3H, s), 0.63-0.54 (2H, m), 0.51-0.44 (2H, m). m/z=511.2 (M+H).

Workup

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

Sources & evidence

ORD record
ord-54003f04842e43a5b2f58b3849b7eae2
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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