1H-Indole-5-Carboxylic Acid → HCID 178521860, compound

HRID 1177645Notes

Reaction equation

HRID 1177645 reaction equation
[NH2:1][C:2]1[C:3](=[S:17])[NH:4][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[NH:18]1[C:26]2[C:21](=[CH:22][C:23]([C:27](O)=[O:28])=[CH:24][CH:25]=2)[CH:20]=[CH:19]1.O.N1(O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.CCOC(C)=O>[SH:17][C:3]1[C:2]([NH:1][C:27]([C:23]2[CH:22]=[C:21]3[C:26](=[CH:25][CH:24]=2)[NH:18][CH:19]=[CH:20]3)=[O:28])=[CH:7][CH:6]=[C:5]([C:8]2([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:10][CH2:9]2)[N:4]=1

Participants

7

Reactant 4

HCID 742801H-Indole-5-Carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 591748363-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione

Product 1

HCID 178521860HCID 178521860, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione (750 mg, 3.10 mmol), 1H-indole-5-carboxylic acid (499 mg, 3.10 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (474 mg, 3.10 mmol), and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (593 mg, 3.10 mmol) in DMF (3.1 mL) was stirred at ambient temperature for 16 h. The reaction mixture was diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with water, washed 2 times with 50 mL of water, separated, dried over sodium sulfate, and concentrated via rotovap to give N-(2-mercapto-6-(1-phenylcyclopropyl)pyridin-3-yl)-1H-indole-5-carboxamide. MS (ESI) m/z: Calculated: 385.1; Observed: 386.4 (M++H).

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with water
  3. washwashed 2 times with 50 mL of water
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-02c72db200ae4c04965c966d56f6a662
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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