Hydrochloric Acid → HCID 19756360, compound

HRID 1587835Notes

Reaction equation

HRID 1587835 reaction equation
Cl.[CH2:2]([C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:29]=[N:30][N:31]([C:33]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:32]=3)=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:52][CH2:53][CH:54]=[O:55])[N:10]=2)[N:5]=1)[CH3:3].N1CC[O:59][CH2:58][CH2:57]1.C([BH3-])#N.[Na+]>C(O)C.CO>[CH2:2]([C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:29]=[N:30][N:31]([C:33]([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:32]=3)=[CH:20][CH:21]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:52][CH2:53][C:54]([O:59][CH2:58][CH3:57])=[O:55])[N:10]=2)[N:5]=1)[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 19756390HCID 19756390, compound

Product 1

HCID 19756360HCID 19756360, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A saturated solution of hydrogen chloride in ethanol (0.1 ml) was added to a solution of compound B (600 mg) and morpholine (450 mg) in methanol (10 ml) containing 3A molecular sieves (1 g). Sodium cyanoborohydride (53 mg) was added and the mixture was stirred for 20 hours. Volatile material was removed by evaporation and the residue purified by flash chromatography, eluting with methanol/ethyl acetate (1:9 v/v). to give 2-ethyl-6-[2-(4-morpholino)ethoxy]-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (A) (152 mg), m.p. 135°-137° C. (after trituration with hexane); NMR (d6 -DMSO): 1.3(t, 3H), 2.3-2.45(m, 4H), 2.6-2.8(m, 2H), 2.85(q, 2H), 3.4-3.55(m, 4H), 4.45-4.6(m, 2H), 5.4(s, 2H), 6.8-6.9(m, 6H), 7.1-7.7(complex m, 18H), 7.8(dd, 1H), 8.15(d, 1H).

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue purified by flash chromatography
  3. washeluting with methanol/ethyl acetate (1:9 v/v)

Sources & evidence

ORD record
ord-cb693278191145d7b8e6d0d39e81d57d
Source dataset
uspto-grants-1993_06
Patent number
US05219863

Reaction notes

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