Hydrochloric Acid → HCID 67734339, compound

HRID 1901820Notes

Reaction equation

HRID 1901820 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][C@@H:6]([CH2:10][NH:11][C:12](=[O:39])[CH2:13][C@@H:14]([C:29]([N:31]([CH:36]2[CH2:38][CH2:37]2)[CH2:32][C:33]([OH:35])=O)=[O:30])[NH:15][S:16]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)(=[O:18])=[O:17])[CH2:5]1)(=[NH:3])[NH2:2].[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N1CCOCC1)C.[ClH:81]>CN(C=O)C>[ClH:81].[NH2:2][C:1](=[NH:3])[N:4]1[CH2:9][CH2:8][CH2:7][C@@H:6]([CH2:10][NH:11][C:12](=[O:39])[CH2:13][C@H:14]([NH:15][S:16]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)(=[O:18])=[O:17])[C:29]([N:31]([CH:36]2[CH2:38][CH2:37]2)[CH2:32][C:33]([N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)=[O:35])=[O:30])[CH2:5]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7525EthylmorpholineHCID 8083MorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6918278Napsagatran

Product 1

HCID 67734339HCID 67734339, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g of N-[N4-[[(S)-1-amidino-3-piperidinyl]methyl]-N2-(2-naphthylsulfonyl)-L-asparaginyl]-N-cyclopropylglycine (Example 4a) is dissolved in 10 ml of DMF, treated with 0.2 ml of morpholine, 0.8 g of BOP and 1.1 ml of 4-ethylmorpholine and stirred at room temperature overnight. The reaction mixture is treated with 20 ml of 1N hydrochloric acid, evaporated and the residue is chromatographed on a RP-18 column with a water-acetonitrile gradient. There is obtained 0.5 g of (S)-N4-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethyl]-N1-cyclopropyl-N1-morpholin-4-ylcarbonylmethyl-2-(naphthalen-2-ylsulfonylamino)-succinamide hydrochloride (1:1), MS (ISP): 628.5 (M+H)+.

Workup

  1. customevaporated
  2. customthe residue is chromatographed on a RP-18 column with a water-acetonitrile gradient

Sources & evidence

ORD record
ord-4e3067ee052a4e74807b8513de80e7e4
Source dataset
uspto-grants-1996_11
Patent number
US05578594

Reaction notes

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