Aminoacetonitrile hydrochloride → HCID 22912917, compound

HRID 1378779Notes

Reaction equation

HRID 1378779 reaction equation
[N:1]1([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]3[CH:18]=[N:19][C:20]([C:21](O)=[O:22])=[C:10]3[CH2:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:25][CH2:26][C:27]#[N:28].C(P(=O)([O-])OCC)#N>ClCCl.C(N(CC)CC)C>[C:26]([CH2:27][NH:28][C:21]([C:20]1[N:19]=[CH:18][N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([C:6]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[O:7])[CH2:9][C:10]=12)=[O:22])#[N:25]

Participants

6

Reactant 3

HCID 11491918Aminoacetonitrile hydrochlorideHCID 22912861HCID 22912861, compoundHCID 86180093Ethyl cyanophosphate

Product 1

HCID 22912917HCID 22912917, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a mixture of 4,5-dihydro-5-[(pyrrolidino)carbonyl]imidazo[1,5-a]quinoxaline-3-carboxylic acid (I, EXAMPLE 323, 0.203 g), 0.060 g of aminoacetonitrile hydrochloride, and 3 ml of dichloromethane are added 0.23 ml of triethylamine and 0.15 ml of ethyl cyanophosphonate. A slight exotherm ensued. After about 45 min a precipitate formed and an additional 5 ml of dichloromethane are added. When the reaction had stirred for a total of 70 min it is partitioned between dichloromethane and aqueous sodium bicarbonate. The organic layers are dried over sodium sulfate and concentrated. The crude product is chromatographed on silica gel (125 ml) eluting with methanol/methylene chloride (2/98), the appropriate fractions are pooled and concentrated to give the title compound, mp 241°-242.5°; MS (m/z) at 350; IR (mineral off) 1641, 1506, 1658, 1409, 1417, 2237 (weak) cm-1 ; NMR (CDCl3) 1.83, 3.31, 4.36, 5.06, 7.12-7.30, 7.40, 7.49, 7.94 δ.

Workup

  1. customAfter about 45 min a precipitate formed
  2. customis partitioned between dichloromethane and aqueous sodium bicarbonate
  3. dry with materialThe organic layers are dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product is chromatographed on silica gel (125 ml)
  6. washeluting with methanol/methylene chloride (2/98)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f937c4260d794503864aa23b5847ab23
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

Loading…