Hydrochloric Acid → HCID 178465189, compound

HRID 1420317Notes

Reaction equation

HRID 1420317 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:17]=[C:16]3[C:12]([N:13]=[CH:14][N:15]3[C@@H:18]3[O:24][C@H:23]([C:25]([NH:27][CH2:28][CH3:29])=[O:26])[C@@H:21]([OH:22])[C@H:19]3[OH:20])=[C:11]([NH:30][CH2:31][CH:32]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:10]=2)[CH2:4][CH2:3]1.[ClH:45].CCOCC>C(O)C>[ClH:45].[NH2:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]2[N:17]=[C:16]3[C:12]([N:13]=[CH:14][N:15]3[C@@H:18]3[O:24][C@H:23]([C:25]([NH:27][CH2:28][CH3:29])=[O:26])[C@@H:21]([OH:22])[C@H:19]3[OH:20])=[C:11]([NH:30][CH2:31][CH:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:10]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 178465188HCID 178465188, compound

Product 1

HCID 178465189HCID 178465189, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (trans)-1-[2-[(4-Aminocyclohexyl)amino]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-1-deoxy-N-ethyl-β-D-ribofuranuronamide (11.05 g, 0.0184 mole) in ethanol (120 ml) was stirred during the addition of 1M hydrogen chloride in ether (18.4 ml, 0.0184 mole). An initial precipitate redissolved on complete addition and the mixture was stirred for 15 min before ether (400 ml) was added. The resulting precipitate was stirred for a further 15 min then collected by filtration under nitrogen and dried in vacuo at 60° over phosphorus pentoxide. The solid (10.1 g) was crystallised from isopropanol (120 ml) to give the title compound (7.95 g). The product had MH+ =601, nmr(δ,DMSO-d6) includes 1.0(t,3H), 1.2-1.5(m,4H), 1.9-2.1(m,4H), 2.9-3.1(m,1H), 3.0-3.3(m,2H), 3.6-3.8(m,1H), 3.9-4.2(m,2H), 4.1-4.2(m,1H), 4.25(s,1H), 4.5-4.6(m,1H), 4.6-4.7(m,1H), 5.4-5.7(m,2H), 5.8(d,1H), 6.2-6.4(m,1H), 7.1-7.4(m,10H), 7.95(bs,1H), 7.8-8.2(m,3H).

Workup

  1. additionwas added
  2. filtrationthen collected by filtration under nitrogen
  3. dry with materialdried in vacuo at 60° over phosphorus pentoxide
  4. customThe solid (10.1 g) was crystallised from isopropanol (120 ml)

Sources & evidence

ORD record
ord-387e2fcb11a04986a770da400539be7f
Source dataset
uspto-grants-1999_03
Patent number
US05889178

Reaction notes

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