Cyclopropylamine → N-{5-[(cyclopropylamino)methyl]-2-methylphenyl}-4-[(4-phenylquinazolin-2-yl)amino]benzamide

HRID 2402498Notes

Reaction equation

HRID 2402498 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:35])=[C:7]([NH:9][C:10](=[O:34])[C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]3[N:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:13][CH:12]=2)[CH:8]=1)=O.[CH:36]1([NH2:39])[CH2:38][CH2:37]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(O)(=O)C.ClCCl>[CH:36]1([NH:39][CH2:1][C:3]2[CH:4]=[CH:5][C:6]([CH3:35])=[C:7]([NH:9][C:10](=[O:34])[C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]4[N:27]=[C:26]([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:12]=3)[CH:8]=2)[CH2:38][CH2:37]1

Participants

7

Reactant 3

HCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57662899N-(5-formyl-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide

Product 1

HCID 57662975N-{5-[(cyclopropylamino)methyl]-2-methylphenyl}-4-[(4-phenylquinazolin-2-yl)amino]benzamideYield 52.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of N-(5-formyl-2-methylphenyl)-4-(4-phenylquinazolin-2-ylamino)benzamide (250 mg, 0.546 mmol), cyclopropylamine (238 μL, 3.44 mmol), dichloromethane (10 m:), tetrahydrofuran (2 drops) and acetic acid (2 drops) was stirred at rt for 1 h. Sodium triacetoxyborohydride (275 mg, 1.30 mmol) was added and the mixture was stirred overnight. The crude reaction was diluted with dichloromethane, washed with saturated sodium bicarbonate and saturated sodium chloride and dried over sodium sulfate. The solution was concentrated on a rotary evaporator and purified by HPLC to give a yellow solid (143 mg, 52%). 1H NMR (400 MHz, DMSO-d6): δ10.32 (s, 1H), 9.69 (s, 1H), 8.17-8.16 (d, 2H), 8.00-7.98 (s, 2H), 7.90-7.86 (m, 3H), 7.85-7.79 (m, 2H), 7.65-7.64 (m, 3H), 7.44-7.40 (t, 1H), 7.31 (s, 1H), 7.20-7.18 (d, 1H), 7.12-7.10 (d, 1H), 3.70 (s, 2H), 2.22 (s, 3H), 2.05 (m, 1H), 0.35-0.32 (m, 2H), 0.27-0.25 (m, 2H). MS (EI) for C32H29N5O: 500.2 (MH+).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe crude reaction
  3. washwashed with saturated sodium bicarbonate and saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationThe solution was concentrated on a rotary evaporator
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-dbc38c8878e2416cbac0387da0554515
Source dataset
uspto-grants-2014_08
Patent number
US08796294B2

Reaction notes

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