Amantadine Hydrochloride → 1-[4-[N-(Adamant-1-yl)carbamoyl]-2-methoxybenzenesulfonyl]-3-cyclohexyl-5-ethoxy-1,3-dihydro-2H-benzimidazol-2-one

HRID 1081506Notes

Reaction equation

HRID 1081506 reaction equation
[CH2:1]([O:3][C:4]1[CH:33]=[CH:32][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([OH:29])=O)=[CH:23][C:22]=3[O:30][CH3:31])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2].Cl.[NH2:35][C:36]12[CH2:45][CH:40]3[CH2:41][CH:42]([CH2:44][CH:38]([CH2:39]3)[CH2:37]1)[CH2:43]2.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:36]12([NH:35][C:27]([C:24]3[CH:25]=[CH:26][C:21]([S:18]([N:8]4[C:7]5[CH:32]=[CH:33][C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]=5[N:10]([CH:11]5[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]5)[C:9]4=[O:17])(=[O:19])=[O:20])=[C:22]([O:30][CH3:31])[CH:23]=3)=[O:29])[CH2:43][CH:42]3[CH2:41][CH:40]([CH2:39][CH:38]([CH2:44]3)[CH2:37]1)[CH2:45]2

Participants

6

Reactant 4

HCID 64150Amantadine HydrochlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 152290425-Ethoxy-1,3-dihydro-1-(2-methoxy-4-carboxybenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-one

Product 1

HCID 233642531-[4-[N-(Adamant-1-yl)carbamoyl]-2-methoxybenzenesulfonyl]-3-cyclohexyl-5-ethoxy-1,3-dihydro-2H-benzimidazol-2-oneYield 42.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound is prepared by the procedure described in EXAMPLE 100 starting from 0.5 g of the compound obtained in EXAMPLE 13, 0.3 g of 1-aminoada- mantane hydrochloride, 0.5 g of BOP, 2 ml of DIPEA and 25 ml of DCM. It is chromatographed on silica using a DCM/MeOH mixture (99/1; v/v) as the eluent to give 0.27 g of the expected product after crystallization from an EtOH/iso ether mixture (80/20; v/v). M.p.=228° C.

Workup

  1. customThis compound is prepared by the procedure
  2. customIt is chromatographed on silica using a DCM/MeOH mixture (99/1; v/v) as the eluent

Sources & evidence

ORD record
ord-4175c1ac464942b48c2ca0fc26602194
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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