2-Amino-2-methyl-1-propanol → 2-(4-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-[1,2,3]triazol-1-yl)-N-(2-hydroxy-1,1-dimethyl-ethyl)-acetamide

HRID 2067207Notes

Reaction equation

HRID 2067207 reaction equation
ClC1C=C(NC2C=CC(F)=CC=2F)C=CC=1C(C1C=C(C2N=NN(CC(NCC)=O)C=2)C=CC=1C)=O.[Cl:37][C:38]1[CH:61]=[C:60]([NH:62][C:63]2[CH:68]=[CH:67][C:66]([F:69])=[CH:65][C:64]=2[F:70])[CH:59]=[CH:58][C:39]=1[C:40]([C:42]1[CH:43]=[C:44]([C:49]2[N:50]=[N:51][N:52]([CH2:54][C:55](O)=[O:56])[CH:53]=2)[CH:45]=[CH:46][C:47]=1[CH3:48])=[O:41].[NH2:71][C:72]([CH3:76])([CH3:75])[CH2:73][OH:74]>>[Cl:37][C:38]1[CH:61]=[C:60]([NH:62][C:63]2[CH:68]=[CH:67][C:66]([F:69])=[CH:65][C:64]=2[F:70])[CH:59]=[CH:58][C:39]=1[C:40]([C:42]1[CH:43]=[C:44]([C:49]2[N:50]=[N:51][N:52]([CH2:54][C:55]([NH:71][C:72]([CH3:76])([CH3:75])[CH2:73][OH:74])=[O:56])[CH:53]=2)[CH:45]=[CH:46][C:47]=1[CH3:48])=[O:41]

Participants

4

Reactant 3

HCID 118072-Amino-2-methyl-1-propanolHCID 11496723(4-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-[1,2,3]triazol-1-yl)-acetic acidHCID 115986752-(4-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-[1,2,3]triazol-1-yl)-N-ethyl-acetamide

Product 1

HCID 116064512-(4-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-[1,2,3]triazol-1-yl)-N-(2-hydroxy-1,1-dimethyl-ethyl)-acetamide

Procedure

The reaction was carried out similarly as described in the preparation of compound 112, using compound 111 (0.08 mmol) and 2-amino-2-methyl-1-propanol (0.08 mmol). The crude product was purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) 50:50 to 100:0 as the eluent to afford the title compound as almost yellow solid. 13C NMR (DMSOd6) δ 8.74 (s, 1H), 8.50 (s, 1H), 7.90 (dd, 1H), 7.85 (bs, 1H), 7.75 (d, 1H), 7.50-7.33 (m, 4H), 7.11 (m, 1H), 6.83 (m, 1H), 6.78 (m, 1H), 5.07 (s, 2H), 4.80 (t, 1H), 3.40 (d, 2H), 2.33 (s, 3H), 1.21 (s, 6H)

Workup

  1. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-477e7188ac0d46efa9b8c88b1a4c6ef7
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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