Triethylamine → HCID 178454038, compound

HRID 1269755Notes

Reaction equation

HRID 1269755 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[NH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH2:15]1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1>CN(C)C=O.O>[C:23]([O:22][C:21](=[O:27])[NH:20][C@H:17]1[CH2:16][CH2:15][C@H:14]([NH:13][C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)=[O:12])[CH2:19][CH2:18]1)([CH3:26])([CH3:24])[CH3:25]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 42484541H-Indazole-5-carboxylic acidHCID 178418300HCID 178418300, compoundHCID 178419079HCID 178419079, compound

Product 1

HCID 178454038HCID 178454038, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the 1H-indazole-5-carboxylic acid (200 mg, 1.23 mmol) obtained in Reference Example 1 in N,N-dimethylformamide (15 ml) were added trans-tert-butyl 4-aminocyclohexylcarbamate (317 mg, 1.48 mmol), triethylamine (0.172 ml, 1.23 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (355 mg, 1.85 mmol) and hydroxybenzotriazole (200 mg, 1.48 mmol), and the resulting mixture was stirred at room temperature for 1 hour. After the reaction solution was heated at 50° C. for 1 hour, water was added thereto at 0° C. The resulting solid was filtered and then dried under reduced pressure to obtain trans-tert-butyl-4-[(1H-indazol-5-ylcarbonyl)amino]cyclohexylcarbamate (435 mg, 98%).

Workup

  1. temperatureAfter the reaction solution was heated at 50° C. for 1 hour
  2. customat 0° C
  3. filtrationThe resulting solid was filtered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-4154019a416148eaab8823f6586daf3f
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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