Diisopropylethylamine → 5-(1-Isopropyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid cyclopropylmethyl-propyl-amide

HRID 901089Notes

Reaction equation

HRID 901089 reaction equation
[CH:1]([N:4]1[CH2:8][CH2:7][CH:6]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([C:19]([OH:21])=O)=[CH:13]3)[CH2:5]1)([CH3:3])[CH3:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH:44]1([CH2:47][NH:48][CH2:49][CH2:50][CH3:51])[CH2:46][CH2:45]1.C(N(C(C)C)C(C)C)C>CN(C=O)C.CO>[CH:44]1([CH2:47][N:48]([CH2:49][CH2:50][CH3:51])[C:19]([C:14]2[NH:15][C:16]3[C:12]([CH:13]=2)=[CH:11][C:10]([O:9][CH:6]2[CH2:7][CH2:8][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:5]2)=[CH:18][CH:17]=3)=[O:21])[CH2:46][CH2:45]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 117787Cyclopropanemethanamine, N-propyl-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 692827665-(1-isopropyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid

Product 1

HCID 692828885-(1-Isopropyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid cyclopropylmethyl-propyl-amideYield 37%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.07 mmol 5-(1-isopropyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid, 1.25 equiv. 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl uronium tetrafluoroborat, 1.25 equivalents cyclopropylmethyl-propyl-amine and 5 equivalents N-ethyldiisopropyl-amine in 0.7 ml DMF was stirred for 16 h at room temperature. The mixture was diluted with 0.8 ml methanol and subjected to preparative HPLC purification on reversed phase material eluting with a gradient of acetonitrile/water/triethyamine. The product fractions were evaporated to dryness to yield 9.1 mg (37%) of the title compound as light brown solid. MS (m/e): 384.5 (MH+, 100%).

Workup

  1. customsubjected to preparative HPLC purification on reversed phase material
  2. washeluting with a gradient of acetonitrile/water/triethyamine
  3. customThe product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-ac605805fa684fcfb9e44dd237ae607d
Source dataset
uspto-grants-2008_04
Patent number
US07361682B2

Reaction notes

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