Diisopropylethylamine → HCID 86729304, compound

HRID 1051544Notes

Reaction equation

HRID 1051544 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]3[NH:15][N:14]=[C:13]([NH2:16])[CH:12]=3)[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.CN1C2C=CC(C3NN=C(N)C=3)=CC=2N=C1.[O:33]1[CH2:35][CH:34]1[CH2:36][N:37]1[CH2:46][CH2:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:38]1.CCN(C(C)C)C(C)C>CCO>[CH2:38]1[C:39]2[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:45][CH2:46][N:37]1[CH2:36][CH:34]([OH:33])[CH2:35][NH:16][C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]3[N:4]=[CH:3][N:2]([CH3:1])[C:6]=3[CH:7]=2)[NH:15][N:14]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 167845312-[(Oxiran-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolineHCID 83639800HCID 83639800, compoundHCID 86729305HCID 86729305, compound

Product 1

HCID 86729304HCID 86729304, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(1-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrazol-3-amine and 5-(1-methyl-1H-benzo[d]imidazol-5-yl)-1H-pyrazol-3-amine (60 mg, 0.27 mmol), 2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline (54 mg, 0.27 mmol) and DIPEA (72 mg, 0.54 mmol) in EtOH (5 mL) was stirred overnight at 120° C. The mixture was concentrated and then purified by prep-HPLC and prep-TLC to give the desired 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-((5-(1-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrazol-3-yl)amino)propan-2-ol (4.5 mg, Yield 4.1%) 1H NMR (400 MHz, MeOD) 8.21-8.16 (m, 1H), 7.86 (s, 1H), 7.71-7.64 (m, 2H), 7.20-7.06 (m, 4H), 5.96 (s, 1H), 4.50-4.39 (m, 1H), 4.29-4.00 (m, 4H), 3.97-3.89 (m, 3H), 3.30-3.11 (m, 2H), 3.08-2.92 (m, 4H). LCMS: RT=0.788 min, M+H+=403.2.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by prep-HPLC and prep-TLC

Sources & evidence

ORD record
ord-680d896648414616a5b7d4eb611ba425
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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