Tert-Butylamine → HCID 46238691, compound

HRID 536553Notes

Reaction equation

HRID 536553 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]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26](O)=[O:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[N:9]=2)=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:52][C:53]([NH2:56])([CH3:55])[CH3:54]>CN(C=O)C.CO>[C:53]([NH:56][C:26]([C:23]1[CH:24]=[CH:25][C:20]([S:17]([N:10]2[C:11](=[O:16])[N:12]([CH:13]3[CH2:14][CH2:15]3)[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:9]2)(=[O:19])=[O:18])=[CH:21][CH:22]=1)=[O:27])([CH3:55])([CH3:54])[CH3:52]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 58460141HCID 58460141, compound

Product 1

HCID 46238691HCID 46238691, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

An amount of 50 mg (0.113 mmol) of the compound from Example 15A was introduced in 1 ml of DMF and admixed with 18 mg (0.136 mmol) of 1-hydroxy-1H-benzotriazole hydrate and with 28 mg (0.147 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride. After 10 minutes of stirring at RT, 2-methylpropan-2-amine (13.1 μl, 0.124 mmol) was added and the mixture was stirred further at room temperature overnight. Subsequently the reaction solution was diluted with methanol and purified by preparative HPLC [Method 5]. This gave 13 mg (24% of theory) of the target compound.

Workup

  1. stirringthe mixture was stirred further at room temperature overnight
  2. custompurified by preparative HPLC [Method 5]

Sources & evidence

ORD record
ord-2350ba2983294a0093db51322dd96202
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

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