HCID 90253536, compound → HCID 90253548, compound

HRID 1478777Notes

Reaction equation

HRID 1478777 reaction equation
[NH2:1][C@@:2]1([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH2:7][O:6][C@@H:5]([C@@H:8]2[CH2:12][CH2:11][CH2:10][O:9]2)[CH2:4][C@H:3]1[CH2:13][OH:14].FC1C=C(F)C=CC=1[C@@]1(N[C:44]([NH:46][C:47](=[O:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[S:45])[C@H](CO)C[C@H]([C@@H]2C[C@H]2C)OC1>>[F:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[C@@:2]1([NH:1][C:44]([NH:46][C:47](=[O:54])[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)=[S:45])[C@H:3]([CH2:13][OH:14])[CH2:4][C@H:5]([C@@H:8]2[CH2:12][CH2:11][CH2:10][O:9]2)[O:6][CH2:7]1

Participants

3

Reactant 2

HCID 90253536HCID 90253536, compoundHCID 118621154HCID 118621154, compound

Product 1

HCID 90253548HCID 90253548, compound

Procedure

{(2R,4R,5S)-5-Amino-5-(2,4-difluorophenyl)-2-[(2S)-tetrahydrofuran-2-yl]tetrahydro-2H-pyran-4-yl}methanol (C101) was converted to the product using the method described for the synthesis of N-({(3S,4R,6R)-3-(2,4-difluorophenyl)-4-(hydroxymethyl)-6-[(1R,2R)-2-methylcyclopropyl]tetrahydro-2H-pyran-3-yl}carbamothioyl)benzamide (C90) in Example 20. Yield: 1.3 g, 2.7 mmol, 70% over 2 steps from (C100). LCMS m/z 477.2 [M+H+].

Sources & evidence

ORD record
ord-a7d8fdb8417b4b288491912eedbc1337
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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