O-Phenylenediamine → HCID 178507510, compound

HRID 1844975Notes

Reaction equation

N1C=CN=[C:2]1[NH:6][C:7]([C:9]1[C:17]2[N:16]=[C:15]([NH:18][C:19]([C:21]3[N:22]=[CH:23][C:24]4[C:29]([CH:30]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:20])[NH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:8].CN(C(O[N:39]1N=N[C:41]2[CH:42]=[CH:43][CH:44]=C[C:40]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1(N)C(N)=CC=CC=1>CN(C=O)C>[NH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:2]=1[NH:6][C:7]([C:9]1[C:17]2[NH:16][C:15]([NH:18][C:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][N:22]=3)=[O:20])=[N:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 0.33 g (1.0 mmol) of -[(isoquinoline-1-carbonyl)-amino]-3H-benzoimidazole-4-carboxylic acid (from Example 58) in DMF (5 mL) was added 0.47 g (1.25 mmol) of HBTU and DIEA (0.5 mL). The mixture was stirred for 5 min, then 0.22 g (2.0 mmol) of benzene-1,2-diamine was added in one portion. The reaction mixture was heated at 50° C. for 1 h, after cooling to room temperature, the coupling product was precipitated by addition of sat. aq. sodium carbonate solution (15 mL). The solid was filtered, washed with water, and dried to provide 0.35 g (80%) of isoquinoline-1-carboxylic acid [7-(2-amino-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-amide. LCMS: 443 (M+1)+.

Workup

temperatureafter cooling to room temperature
customthe coupling product was precipitated by addition of sat. aq. sodium carbonate solution (15 mL)
filtrationThe solid was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-703d2dbfd8b844929de759c1924d4d6f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946259B2

Reaction notes

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