Diisopropylethylamine → HCID 178490989, compound

HRID 2200912Notes

Reaction equation

HRID 2200912 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:5][NH:6][C:7]1[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[C:9]([N:16]2[CH2:24][C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:17]2)[N:8]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:63][C@H:64]1[CH2:69][CH2:68][C@H:67]([OH:70])[CH2:66][CH2:65]1>CN(C=O)C.O>[OH:70][C@H:67]1[CH2:68][CH2:69][C@H:64]([NH:63][C:13]([C:12]2[C:7]([NH:6][CH2:5][C:4]3[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:2]([Cl:1])[CH:3]=3)=[N:8][C:9]([N:16]3[CH2:24][C:23]4[C:18](=[N:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)=[N:10][CH:11]=2)=[O:15])[CH2:65][CH2:66]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1181575174-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)yl)-5-pyrimidine carboxylic acidHCID 178511715HCID 178511715, compound

Product 1

HCID 178490989HCID 178490989, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In DMF (10 mL) was dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)yl)-5-pyrimidine formic acid (0.8 g, 1.94 mmol). The solution was cooled in an ice bath. HATU (1.11 g, 2.91 mmol) and DIPEA (0.37 g, 2.87 mmol) were added. After 20 min, trans-4-aminocyclohexanol (0.27 g, 2.3 mmol) was added in batches. The reaction was conducted overnight. LC-MS was used to monitor the reaction. The reaction mixture was poured into water (50 mL) and filtrated. The solid was recrystallized with acetone (20 mL) to give N-((trans)-4-hydroxycyclohexan-1-yl)-4-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)yl)-5-pyrimidine formamide (300 mg, 30.3% yield).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. waitThe reaction was conducted overnight
  3. customthe reaction
  4. filtrationfiltrated
  5. customThe solid was recrystallized with acetone (20 mL)

Sources & evidence

ORD record
ord-beff835950fb4d5eb9c049fdf614f80e
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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