Ammonia → HCID 90014477, compound

HRID 930965Notes

Reaction equation

HRID 930965 reaction equation
[N:1]([CH2:4][CH:5]1[CH2:10][CH2:9][C:8]2[C:11]3[C:16]([NH:17][C:18]4[CH:27]=[CH:26][C:21]5[NH:22][C:23](=[O:25])[S:24][C:20]=5[CH:19]=4)=[N:15][CH:14]=[N:13][C:12]=3[S:28][C:7]=2[CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N>O1CCCC1>[NH2:1][CH2:4][CH:5]1[CH2:10][CH2:9][C:8]2[C:11]3[C:16]([NH:17][C:18]4[CH:27]=[CH:26][C:21]5[NH:22][C:23](=[O:25])[S:24][C:20]=5[CH:19]=4)=[N:15][CH:14]=[N:13][C:12]=3[S:28][C:7]=2[CH2:6]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 90014762HCID 90014762, compound

Product 1

HCID 90014477HCID 90014477, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture comprising 1.78 g (4.35 mmol) (RS)-6-{[7-(azidomethyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl]amino}-1,3-benzothiazol-2(3H)-one (prepared according to example 19), 70 mL tetrahydrofuran and 2.54 g triphenylphosphine was stirred at 23° C. for 2 hours, 9.3 mL aqueous ammonia (25%) were added and stirring continued overnight. The solvents were removed and the residue was purified by chromatography to give 1.04 g (59%) of the title compound.

Workup

  1. customThe solvents were removed
  2. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-6090f9bbe5924d38a49626571ab408fb
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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