Isobutyryl chloride → HCID 57550089, compound

HRID 1518486Notes

Reaction equation

HRID 1518486 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]3[CH2:20][CH2:19][N:18]([C:21]4[N:26]=[CH:25][C:24]([CH2:27][CH2:28][CH3:29])=[CH:23][N:22]=4)[CH2:17][CH2:16]3)=[CH:10][C:9]2=[O:30])=[CH:4][C:3]=1[F:31].NC1C=CC(N2C=CC(OC3CCN(C4N=[CH:56][C:55]([CH2:58]CC)=[CH:54]N=4)CC3)=CC2=O)=CC=1.[C:62](Cl)(=[O:66])C(C)C>>[F:31][C:3]1[CH:4]=[C:5]([N:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]3[CH2:16][CH2:17][N:18]([C:21]4[N:26]=[CH:25][C:24]([CH2:27][CH2:28][CH3:29])=[CH:23][N:22]=4)[CH2:19][CH2:20]3)=[CH:10][C:9]2=[O:30])[CH:6]=[CH:7][C:2]=1[NH:1][C:62](=[O:66])[C:55]([CH3:54])([CH3:56])[CH3:58]

Participants

4

Reactant 3

HCID 62325Isobutyryl chlorideHCID 57468433HCID 57468433, compoundHCID 57468447HCID 57468447, compound

Product 1

HCID 57550089HCID 57550089, compound

Procedure

Example 239 was prepared according to procedures described in Example 208 substituting 1-(4-amino-3-fluorophenyl)-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one for 1-(4-aminophenyl)-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one and substituting pivaloyl chloride (Aldrich) for Isobutyryl chloride except that the crude solid purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2). 1H NMR (400 MHz, CDCl3) δ ppm 8.51 (t, J=8.66 Hz, 1 H), 8.19 (s, 2 H), 7.68 (d, J=3.51 Hz, 1 H), 7.25-7.30 (m, 1 H), 7.17-7.25 (m, 1 H), 7.12 (d, J=8.78 Hz, 1 H), 5.96-6.06 (m, 2H), 4.51-4.63 (m, 1 H), 4.15-4.26 (m, 2 H), 3.59-3.69 (m, 2H), 2.43 (t, J=7.53 Hz, 2 H), 1.97-2.15 (m, 2H), 1.79-1.97 (m, 2 H), 1.54-1.65 (m, 2 H), 1.36 (s, 9 H), 0.96 (t, J=7.28 Hz, 3 H). MS (ESI) 508 (M+H).

Workup

  1. customExample 239 was prepared
  2. custompurified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-70f18be132fc45349df2c81245c9ed75
Source dataset
uspto-grants-2012_07
Patent number
US08232404B2

Reaction notes

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