Triethylamine → HCID 178522415, compound

HRID 2064623Notes

Reaction equation

HRID 2064623 reaction equation
FC(F)[O:3][C:4]1[CH:26]=[CH:25][C:7]2NC(C3C(NC(N4CCCCC4)=O)=CNN=3)=NC=2C=1.[NH:28]1[C:39]2[C:31](=[CH:32][C:33]3[CH2:34][CH2:35][CH2:36][C:37]=3[CH:38]=2)[N:30]=[C:29]1[C:40]1[C:44]([NH2:45])=[CH:43][NH:42][N:41]=1.C(N(CC)CC)C.C1(C(Cl)=O)CC1.[OH-].[K+].[Cl-].[NH4+]>O1CCCC1>[NH:30]1[C:31]2[C:39](=[CH:38][C:37]3[CH2:36][CH2:35][CH2:34][C:33]=3[CH:32]=2)[N:28]=[C:29]1[C:40]1[C:44]([NH:45][C:4]([CH:26]2[CH2:7][CH2:25]2)=[O:3])=[CH:43][NH:42][N:41]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 178508051HCID 178508051, compoundHCID 178522444HCID 178522444, compound

Product 1

HCID 178522415HCID 178522415, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

By proceeding in a similar manner to Example 258(a) above but (i) treating a solution of 3-(1,5,6,7-tetrahydro-1,3-diaza-s-indacen-2-yl)-1H-pyrazol-4-ylamine [310 mg, Example 256(b)] and triethylamine (4 eq) in tetrahydrofuran (15 mL) with cyclopropanecarbonyl chloride (4 eq), (ii) stirring the reaction mixture at 60° C. for 2 hours, (iii) treating the resulting bis-acylated product with methanolic potassium hydroxide (20 mL, 10.05 g KOH) at 40° C. for 1 hour followed by treatment with aqueous ammonium chloride (200 mL), (iii) extracting this mixture three times with ethyl acetate (100 mL), (iv) evaporating the combined extracts and (v) chromatographing the residue on silica gel (ethyl acetate/gradient of 50-0% heptane) there was prepared cyclopropanecarboxylic acid [3-(1,5,6,7-tetrahydro-1,3-diaza-s-indacen-2-yl)-1H-pyrazol-4-yl]amide (50 mg) as a yellow solid. LC-MS (Method E) RT=2.05 minutes, 308 (M+H)+.

Workup

  1. extractionextracting this mixture three times with ethyl acetate (100 mL), (iv)
  2. customevaporating the combined extracts and (v) chromatographing the residue on silica gel (ethyl acetate/gradient of 50-0% heptane) there
  3. customwas prepared cyclopropanecarboxylic acid [3-(1,5,6,7-tetrahydro-1,3-diaza-s-indacen-2-yl)-1H-pyrazol-4-yl]amide (50 mg) as a yellow solid

Sources & evidence

ORD record
ord-700ab96b803142cc9a16ff22c6550e8f
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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