Cumylamine → HCID 58012229, compound

HRID 660920Notes

Reaction equation

HRID 660920 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18](O)=[O:19])[N:9]=2)=[CH:4][CH:3]=1.[C:21]1([C:27]([NH2:30])([CH3:29])[CH3:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:30][C:27]([CH3:29])([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:28])=[O:19])[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 68509Cumylamine2×HCID 757711-Hydroxybenzotriazole2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 42632357[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid

Product 1

HCID 58012229HCID 58012229, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

70.0 mg (0.238 mmol) of [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid from Example 88A and 32.2 mg (0.238 mmol) of 2-phenylpropan-2-amine are placed in 2 ml of dimethylformamide and treated with 38.7 mg (0.286 mmol) of HOBt. After 10 mins' stirring, 59.4 mg (0.310 mmol) EDC hydrochloride are added and the mixture is stirred overnight at room temperature. After this, 32.2 mg (0.238 mmol) of 2-phenylpropan-2-amine, 38.7 mg (0.286 mmol) of HOBt and 59.4 mg (0.310 mmol) of EDC hydrochloride are again added to the reaction mixture and stirred for a further for two hours at room temperature. Without further workup, the mixture is purified directly by preparative HPLC [Method 10]. 44 mg (45% of theory) of the target compound are thus obtained.

Workup

  1. stirringthe mixture is stirred overnight at room temperature
  2. stirringstirred for a further for two hours at room temperature
  3. customWithout further workup, the mixture is purified directly by preparative HPLC [Method 10]
  4. custom44 mg (45% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-16333ab8127541a69114837f3e94ce43
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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