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

HRID 656443Notes

Reaction equation

HRID 656443 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-f5b138ae44d5436f83df546a6858dff9
Source dataset
uspto-grants-2011_12
Patent number
US08071762B2

Reaction notes

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