Diisopropylethylamine → HCID 69201486, compound

HRID 270743Notes

Reaction equation

HRID 270743 reaction equation
[NH2:1][C@H:2]([CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[C:15]([CH3:17])[CH:16]=1)[NH:13][N:12]=[CH:11]2)[C:3]([O:5][CH3:6])=[O:4].C(N(C(C)C)CC)(C)C.C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:29](=[O:30])C1.[NH:45]1[CH2:50][CH2:49][CH:48]([N:51]2[CH2:60][C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[NH:53][C:52]2=[O:61])[CH2:47][CH2:46]1>CN(C)C=O>[CH3:6][O:5][C:3](=[O:4])[C@H:2]([NH:1][C:29]([N:45]1[CH2:46][CH2:47][CH:48]([N:51]2[CH2:60][C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[NH:53][C:52]2=[O:61])[CH2:49][CH2:50]1)=[O:30])[CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[C:15]([CH3:17])[CH:16]=1)[NH:13][N:12]=[CH:11]2

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 676246Di(succinimido) carbonateHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 59833953Methyl (αR)-α-amino-7-methyl-1H-indazole-5-propanoate

Product 1

HCID 69201486HCID 69201486, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-methyl 2-amino-3-(7-methyl-1H-indazol-5-yl)propanoate (1.07 g, 4 mmol) and diisopropylethylamine (2.09 mL, 12 mmol) in dimethylformamide (15 mL) at room temperature was added N,N-disuccinimidyl carbonate (0.52 g, 4 mmol). The resulting mixture was stirred at room temperature for 30 min and treated with 3-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one (0.92 g, 4 mmol) in portions. The reaction was stirred for 24 h. The mixture was concentrated, and the residue was purified by flash chromatography (silica gel, 30:1 dichloromethane/methanol 60:1, 30:1) to give 2 g (100%). Mass spec.: 491.38 (MH)+, HPLC tR=2.25.

Workup

  1. stirringThe reaction was stirred for 24 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by flash chromatography (silica gel, 30:1 dichloromethane/methanol 60:1, 30:1)
  4. customto give 2 g (100%)

Sources & evidence

ORD record
ord-cdf4fa05d76d4a538e5bc646c256b1b5
Source dataset
uspto-grants-2008_11
Patent number
US07449586B2

Reaction notes

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