Methylamine → HCID 67236301, compound

HRID 1748358Notes

Reaction equation

HRID 1748358 reaction equation
[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([NH:18][C:19]4[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=4[C:21]([OH:23])=O)=[O:17])=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.CN.C1COCC1.O[N:36]1[C:40]2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C(N=C=NCCCN(C)C)C>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH3:40][NH:36][C:21]([C:20]1[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=1[NH:18][C:16]([C:13]1[CH:12]=[CH:11][C:10]2[CH:9]=[C:8]3[C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH2:6][N:7]3[C:15]=2[CH:14]=1)=[O:17])=[O:23]

Participants

9

Reactant 6

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67235916HCID 67235916, compound

Product 1

HCID 67236301HCID 67236301, compoundYield 106.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{[(1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indol-8-yl)carbonyl]amino}benzoic acid (100 mg, 0.28 mmol) in DMF (1.0 mL) are added 2M methylamine in THF (0.69 mL, 1.38 mmol), N-hydroxybenzotriazole (26 mg, 0.20 mmol), N,N-diisopropylethylamine (0.10 mL, 0.55 mmol) and 4-dimethylaminopyridine (6.7 mg, 0.06 mmol). After the reaction mixture is stirred for 10 min, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (158 mg, 0.83 mmol) is added. The reaction mixture is then stirred for another 16 h at room temperature. The crude reaction mixture is purified by preparative HPLC using 10-85% acetonitrile/water with 0.1% TFA to afford the title compound (80 mg, 77%). LCMS (ESMS): m/z 377.20 (M+H+).

Workup

  1. stirringThe reaction mixture is then stirred for another 16 h at room temperature
  2. customThe crude reaction mixture
  3. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-9144ff75d71c41efa8583c4bf9a6d701
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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