Hydrochloric Acid → 5-[(4aR,7aR)-2-Amino-6-[5-fluoro-4-(2-hydroxypropan-2-yl)pyrimidin-2-yl]-4a,5,6,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a(4H)-yl]thiophene-2-carbonitrile hydrochloride

HRID 338173Notes

Reaction equation

HRID 338173 reaction equation
[NH2:1][C:2]1[S:3][CH2:4][C@@H:5]2[CH2:10][N:9]([C:11]3[N:16]=[C:15]([C:17]([OH:20])([CH3:19])[CH3:18])[C:14]([F:21])=[CH:13][N:12]=3)[CH2:8][C@:6]2([C:22]2[S:26][C:25]([C:27]#[N:28])=[CH:24][CH:23]=2)[N:7]=1.[ClH:29]>C(OCC)C>[ClH:29].[NH2:1][C:2]1[S:3][CH2:4][C@@H:5]2[CH2:10][N:9]([C:11]3[N:16]=[C:15]([C:17]([OH:20])([CH3:19])[CH3:18])[C:14]([F:21])=[CH:13][N:12]=3)[CH2:8][C@:6]2([C:22]2[S:26][C:25]([C:27]#[N:28])=[CH:24][CH:23]=2)[N:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 867622495-[(4aR,7aR)-2-Amino-6-[5-fluoro-4-(2-hydroxypropan-2-yl)pyrimidin-2-yl]-4a,5,6,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a(4H)-yl]thiophene-2-carbonitrile

Product 1

HCID 867622555-[(4aR,7aR)-2-Amino-6-[5-fluoro-4-(2-hydroxypropan-2-yl)pyrimidin-2-yl]-4a,5,6,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a(4H)-yl]thiophene-2-carbonitrile hydrochlorideYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of the 5-[(4aR,7aR)-2-amino-6-[5-fluoro-4-(2-hydroxypropan-2-yl)pyrimidin-2-yl]-4a,5,6,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a(4H)-yl]thiophene-2-carbonitrile (256 mg, 612 μmol) in diethyl ether (20 mL) is added a solution of 1 M HCl in diethyl ether (673 μL, 0.673 mmol). The resulting white mixture is stirred for a few minutes, and then the solid is collected by vacuum filtration, and is rinsed with diethyl ether, to give the title compound (201 mg, 72%) as a white solid. MS/ES (m/z) 419.2 (M+H).

Workup

  1. filtrationthe solid is collected by vacuum filtration
  2. washis rinsed with diethyl ether

Sources & evidence

ORD record
ord-92c5344698954fb88ea22fb76e0906fd
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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