4-(Tert-butoxy)aniline → (R)-N-(4-(tert-Butoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinamide

HRID 924094Notes

Reaction equation

HRID 924094 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:15]([C:16]3[CH:17]=[N:18][CH:19]=[N:20][CH:21]=3)=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=2)[CH2:3]1.[C:22]([O:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1)([CH3:25])([CH3:24])[CH3:23]>>[C:22]([O:26][C:27]1[CH:28]=[CH:29][C:30]([NH:31][C:11](=[O:13])[C:10]2[CH:14]=[C:15]([C:16]3[CH:17]=[N:18][CH:19]=[N:20][CH:21]=3)[C:7]([N:4]3[CH2:5][CH2:6][C@@H:2]([OH:1])[CH2:3]3)=[N:8][CH:9]=2)=[CH:32][CH:33]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

3

Reactant 2

HCID 111595184-(Tert-butoxy)anilineHCID 118195186(R)-6-(3-Hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinic acid

Product 1

HCID 89908086(R)-N-(4-(tert-Butoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described infashion to that described in Example 170 using (R)-6-(3-hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinic acid (Stage 170.1) and 4-tert-butoxyaniline to afford an off-white foam. HPLC (Condition 4) tR=4.31 min, UPLC-MS (Condition 3) tR=0.84 min, m/z=434.4 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.26 (s, 9H) 1.67-1.77 (m, 1H) 1.79-1.91 (m, 1H) 2.88 (d, J=3.91 Hz, 1H) 3.14-3.25 (m, 2H) 3.30-3.45 (m, 1H) 4.14-4.24 (m, 1H) 4.86 (d, J=3.52 Hz, 1H) 6.88-7.00 (m, 2H) 7.56-7.66 (m, 2H) 8.07 (d, J=2.35 Hz, 1H) 8.76 (d, J=2.35 Hz, 1H) 8.87 (d, J=0.78 Hz, 2H) 9.17 (s, 1H) 9.92 (s, 1H).

Workup

  1. customto afford an off-white foam

Sources & evidence

ORD record
ord-df63777e0b104501bd2abd48fa1f268d
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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