1,3-Cyclohexanediamine → HCID 86678005, compound

HRID 246704

Reaction equation

HRID 246704 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:11]([OH:13])=O)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH:14]1([NH2:21])[CH2:19][CH2:18][CH2:17][CH:16]([NH2:20])[CH2:15]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:20][CH:16]1[CH2:17][CH2:18][CH2:19][CH:14]([NH:21][C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([Br:1])[N:3]=3)[NH:8][CH:9]=2)=[O:13])[CH2:15]1

Participants

6

Reactant 4

HCID 188141,3-CyclohexanediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866778972-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Product 1

HCID 86678005HCID 86678005, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.2 g, 0.83 mmol), cyclohexane-1,3-diamine (0.473 g, 4.15 mmol), HATU (0.475 g, 1.25 mmol), DIPEA (0.322 g, 2.5 mmol) in 15 mL of DMF were stirred at room temperature overnight. The solvent was removed under reduced pressure at 70° C. to give N-(3-aminocyclohexyl)-2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide as a crude which was used to the next step without further purification. MS: (M+H)+=338.1.

Workup

  1. customThe solvent was removed under reduced pressure at 70° C.

Sources & evidence

ORD record
ord-399e91d6b945443188c43a9458f89d22
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

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