Diisopropylethylamine → 4-{3-[5-(2-Methoxy-1,1-dimethyl-ethyl)-indan-1-yl]-ureido}-indazole-1-carboxylic acid methyl ester

HRID 451611Notes

Reaction equation

HRID 451611 reaction equation
[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[C:9]([NH:14][C:15]([O:17]N3C(=O)CCC3=O)=O)[CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6]1)=[O:4].[CH3:25][O:26][CH2:27][C:28]([C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[CH:36]([NH2:40])[CH2:35][CH2:34]2)([CH3:30])[CH3:29].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[C:9]([NH:14][C:15]([NH:40][CH:36]3[C:37]4[C:33](=[CH:32][C:31]([C:28]([CH3:30])([CH3:29])[CH2:27][O:26][CH3:25])=[CH:39][CH:38]=4)[CH2:34][CH2:35]3)=[O:17])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6]1)=[O:4]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 11313556methyl 4-({[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}amino)-1H-indazole-1-carboxylateHCID 671874325-(2-Methoxy-1,1-dimethyl-ethyl)-indan-1-ylamine

Product 1

HCID 671881034-{3-[5-(2-Methoxy-1,1-dimethyl-ethyl)-indan-1-yl]-ureido}-indazole-1-carboxylic acid methyl esterYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(2,5-dioxo-pyrrolidin-1-yloxycarbonylamino)-indazole-1-carboxylic acid methyl ester (0.66 g, 2.00 mmol) was added to a solution of 5-(2-methoxy-1,1-dimethyl-ethyl)-indan-1-ylamine (0.46 g, 2.1 mmol) and diisopropylethylamine (0.26 g, 2.00 mmol) in DMF (6 mL) under nitrogen atmosphere at ambient temperature. After 30 minutes the mixture was diluted with water (6 mL). The resulting precipitate was filtered off, washed with aqueous MeCN twice and dried to obtain desired product (0.48 g, 55%). NMR (DMSO-d6): 8.82 (s, 1H), 8.40 (s, 1H), 7.95 (s, 1H), 7.88 (d, J 7.5 Hz, 1H), 7.69 (d, J 8 Hz, 1H), 7.52 (t, J 8 Hz, 1H), 7.24 (m, 2H), 6.70 (d, J 7.5 Hz, 1H), 5.18 (m, 1H), 4.02 (m, 3H), 3.38 (s, 2H), 3.20 (s, 3H), 3.10-2.72 (m, 2H), 2.42 (m, 1H), 1.83 (m, 1H), 1.14 (s, 6H). MS (DCI): 437 (M+1).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with aqueous MeCN twice
  3. customdried

Sources & evidence

ORD record
ord-436ba7bc9d8941a0b770808ac743f7d2
Source dataset
uspto-grants-2013_07
Patent number
US08487116B2

Reaction notes

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