Nicotinic Acid → HCID 13079768, compound

HRID 2295328Notes

Reaction equation

HRID 2295328 reaction equation
Cl.C(N=C=NCCCN(C)C)C.Cl.NC[C:16]([NH:18][C@@H:19]1[CH2:38][CH2:37][C@@:36]2([CH3:39])[C@@H:21]([CH2:22][CH2:23][C@@H:24]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:40])[C@H:25]3[CH2:26][CH2:27][C@@H:28]2[CH:29]([OH:31])[CH3:30])[CH2:20]1)=[O:17].[NH2:41][C@@H:42]1CC[C@@]2(C)[C@@H:44]([CH2:45][CH2:46][C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2C(O)C)[CH2:43]1.C(O)(=O)C1C=CC=NC=1>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:30][C@H:29]([OH:31])[C@@H:28]1[C@:32]2([CH3:40])[C@H:25]([C@H:24]3[C@H:35]([CH2:34][CH2:33]2)[C@:36]2([CH3:39])[C@H:21]([CH2:20][C@H:19]([NH:18][C:16]([C:45]4[CH:46]=[N:41][CH:42]=[CH:43][CH:44]=4)=[O:17])[CH2:38][CH2:37]2)[CH2:22][CH2:23]3)[CH2:26][CH2:27]1

Participants

7

Reactant 4

HCID 938Nicotinic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 22825173HCID 22825173, compoundHCID 70524041HCID 70524041, compound

Product 1

HCID 13079768HCID 13079768, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

582 mg of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride were added under an inert atmosphere to a solution of 960 mg of (20S) 3α-amino-5α-pregnane-20-ol, 813 mg of nicotinic acid, 30 ml of chloroform and 6 ml of pyridine and after 31/2 hours, another 291 mg of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride were added to the mixture. The mixture was stirred for 16 hours and was evaporated to dryness. The residue was taken up in 30 ml of water and the solution was iced and vacuum filtered. The product was washed with water, dried at 80° C. under reduced pressure and was crystallized from methanol to obtain 920 mg of N-[(20S) 5α-pregnan-20-ol-3α-yl]-3-pyridinecarboxamide melting at 258° C. and having a specific rotation of [α]D20 =+14.5± 1° (c=1% in pyridine).

Workup

  1. customwas evaporated to dryness
  2. filtrationvacuum filtered
  3. washThe product was washed with water
  4. customdried at 80° C. under reduced pressure
  5. customwas crystallized from methanol

Sources & evidence

ORD record
ord-64cb41568c524ae0ac61f66bdee705b7
Source dataset
uspto-grants-1984_01
Patent number
US04424218

Reaction notes

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