Triethylamine → HCID 178473460, compound

HRID 968229Notes

Reaction equation

HRID 968229 reaction equation
[CH2:1]([O:3][C:4]([N:6]=[C:7]=S)=[O:5])[CH3:2].[NH2:9][C:10]1[C:11]([NH:26][C@H:27]([CH3:30])[CH2:28][OH:29])=[N:12][C:13]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])=[N:14][C:15]=1[NH2:16].C(N(CC)CC)C.C(N=C=NC(C)C)(C)C>C(#N)C>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][S:17][C:13]1[N:14]=[C:15]2[C:10]([N:9]=[C:7]([NH:6][C:4](=[O:5])[O:3][CH2:1][CH3:2])[NH:16]2)=[C:11]([NH:26][C@H:27]([CH3:30])[CH2:28][OH:29])[N:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12734DiisopropylcarbodiimideHCID 85320Ethyl isothiocyanatoformateHCID 69749516(2R)-2-[[5,6-diamino-2-[[(2-fluorophenyl)methyl]thio]-4-pyrimidinyl]amino]-1-propanol

Product 1

HCID 178473460HCID 178473460, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of ethoxycarbonylisothiocyanate (0.48 ml) in dry acetonitrile (20 ml) at 0° C. under an atmosphere of nitrogen was added a suspension of the product from example 4, step (e) (1.15 g) in dry acetonitrile (20 ml) containing 2.5 eq triethylamine. After stirring at 0° C. for 5 min, diisopropylcarbodiimide (0.8 ml) was added and the reaction warmed to 70° C. for 1 hr. The reaction mixture was concentrated in vacuo and the residue purified twice by silica gel chromatography, eluting both times with 3:1 ethyl acetate:DCM, to afford the subtitled product as a white solid (0.045 g).

Workup

  1. temperaturethe reaction warmed to 70° C. for 1 hr
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue purified twice by silica gel chromatography
  4. washeluting both times with 3:1 ethyl acetate

Sources & evidence

ORD record
ord-b8c87a5279e847e5af7e96342a4a88ba
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

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