HCID 74983199, compound → HCID 74983200, compound

HRID 1915917Notes

Reaction equation

NC1SC(C2C(F)=CC=CC=2F)=NC=1C(NC1C=NN(C)C=1N1CCC[C@H](NCCO)CC1)=O.[OH:35][CH2:36][CH2:37][N:38]([CH2:76][CH2:77][OH:78])[C@@H:39]1[CH2:45][CH2:44][CH2:43][N:42]([C:46]2[N:50]([CH3:51])[N:49]=[CH:48][C:47]=2[NH:52][C:53]([C:55]2[N:56]=[C:57]([C:68]3[C:73]([F:74])=[CH:72][CH:71]=[CH:70][C:69]=3[F:75])[S:58][C:59]=2[NH:60]C(=O)OC(C)(C)C)=[O:54])[CH2:41][CH2:40]1>>[NH2:60][C:59]1[S:58][C:57]([C:68]2[C:69]([F:75])=[CH:70][CH:71]=[CH:72][C:73]=2[F:74])=[N:56][C:55]=1[C:53]([NH:52][C:47]1[CH:48]=[N:49][N:50]([CH3:51])[C:46]=1[N:42]1[CH2:43][CH2:44][CH2:45][C@H:39]([N:38]([CH2:37][CH2:36][OH:35])[CH2:76][CH2:77][OH:78])[CH2:40][CH2:41]1)=[O:54]

Participants

Reactant 2

HCID 74983199HCID 74983199, compound

HCID 89456404HCID 89456404, compound

Product 1

HCID 74983200HCID 74983200, compoundYield 71%

Procedure

In the preparation of 335, tert-butyl N-[4-[[5-[(4R)-4-[bis(2-hydroxyethyl)amino]azepan-1-yl]-1-methyl-pyrazol-4-yl]carbamoyl]-2-(2,6-difluorophenyl)thiazol-5-yl]carbamate was deprotected following the procedure in Example 334 to give 336 (6 mg, 71%). 1H NMR (400 MHz, DMSO) δ 8.63 (s, 1H), 8.24 (s, 1H), 7.56 (s, 1H), 7.55-7.41 (m, 3H), 7.27 (t, J=8.7 Hz, 2H), 3.65 (s, 3H), 3.19-3.02 (m, 7H), 2.85-2.71 (m, 2H), 2.46 (t, J=6.2 Hz, 4H), 1.92-1.75 (m, 3H), 1.67-1.50 (m, 3H). LCMS (ES+) m/z 536 (M+1)

Sources & evidence

ORD record: ord-ec50ebaa86be44468caed6197de9a1dc
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614206B2

Reaction notes

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