Sodium Carbonate → HCID 13983098, compound

HRID 893687Notes

Reaction equation

Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][CH2:12][OH:13].[NH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:24]2[N:28]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:27]3[CH:37]=[CH:38][CH:39]=[CH:40][C:26]=3[N:25]=2)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+]>O>[F:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][N:28]2[C:27]3[CH:37]=[CH:38][CH:39]=[CH:40][C:26]=3[N:25]=[C:24]2[NH:23][CH:20]2[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][NH:14][C:2]3[N:10]=[CH:9][N:8]=[C:7]4[C:3]=3[N:4]=[CH:5][N:6]4[CH2:11][CH2:12][OH:13])[CH2:18][CH2:19]2)=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2 parts of 6-chloro-9H-purine-9-ethanol, 3.7 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine, 1.06 parts of sodium carbonate and 45 parts of N;N-dimethylacetamide was stirred and heated for 3 hours at 130° C. The reaction mixture was poured into water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 2.8 parts (53%) of 6-[[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]amino]-9H-purine-9-ethanol; mp. 168.7° C. (compound 93).

Workup

extractionthe product was extracted with 4-methyl-2-pentanone
customThe extract was dried
filtrationfiltered
customevaporated
customThe residue was crystallized from acetonitrile
filtrationThe product was filtered off
customdried

Sources & evidence

ORD record: ord-7641729f5b24415ca2eb198f92359283
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05126339

Reaction notes

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