HCID 68675669, compound → Ammonia

HRID 1716263Notes

Reaction equation

F[C:2](F)(F)[C:3]([OH:5])=O.[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])[CH2:16][CH2:15]1.I.[NH2:27][C:28]1[C:29]([C:36]([NH:38][C:39](=[NH:42])SC)=[O:37])=[N:30][C:31]([Cl:35])=[C:32]([NH2:34])[N:33]=1>CN(C=O)C.CO>[NH3:8].[NH2:27][C:28]1[C:29]([C:36]([NH:38][C:39]([NH:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][N:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:39]([NH2:42])=[N:38][C:3]([C:2]3[C:28]([NH2:27])=[N:33][C:32]([NH2:34])=[C:31]([Cl:35])[N:30]=3)=[O:5])[CH2:15][CH2:16]2)=[NH:42])=[O:37])=[N:30][C:31]([Cl:35])=[C:32]([NH2:34])[N:33]=1

Participants

Conditions

Temperature: 50 °C

Procedure

5-[4-(5-Amino-pentyl)-piperazin-1-yl]pentylamine trifluoroacetate (Intermediate P) (172 mg, 0.24 mmol) is added to a stirring solution of 1-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-2-methyl-isothiourea hydroiodide (93 mg, 0.48 mmol) in DMF (1 mL). The resulting mixture is heated to 50° C. for 8 hours and then allowed to cool to RT. The reaction mixture is quenched with 5% citric acid solution and addition of DCM results in the formation of a gum. The gum is isolated and dissolved in MeOH (2 mL). The solution is passed through a “capture release” SCX-2 cartridge eluting with 1 N ammonia in MeOH followed by 1:1 MeOH:ammonia solution to afford the title compound.

Workup

temperatureto cool to RT
customThe reaction mixture is quenched with 5% citric acid solution and addition of DCM
customresults in the formation of a gum
customThe gum is isolated
washeluting with 1 N ammonia in MeOH

Sources & evidence

ORD record: ord-8bb354001b224cad9e29741dab652d8e
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803804B2

Reaction notes

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