4-Amino-1-methylpiperidine → HCID 131734927, compound

HRID 921547Notes

Reaction equation

HRID 921547 reaction equation
BrC1C=C([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][C:18]([C:19]4[CH:20]=[N:21][C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[C:13]3[C:12]([CH2:29][CH3:30])=[CH:11]2)C=CC=1C#N.NC1CCN(C)CC1.C(C1C2C(=NC=CC=2C2C=NC3C(C=2)=CC=CC=3)N([C:60]2[CH:67]=[CH:66][C:63]([C:64]#[N:65])=[C:62]([NH:68][CH:69]3[CH2:74][CH2:73][N:72]([CH3:75])[CH2:71][CH2:70]3)[CH:61]=2)C=1)C>>[CH2:29]([C:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][C:18]=2[C:19]2[CH:20]=[N:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:10]([C:61]2[C:62]([NH:68][CH:69]3[CH2:74][CH2:73][N:72]([CH3:75])[CH2:71][CH2:70]3)=[C:63]([CH:66]=[CH:67][CH:60]=2)[C:64]#[N:65])[CH:11]=1)[CH3:30]

Participants

4

Reactant 3

HCID 27375314-Amino-1-methylpiperidineHCID 67500944HCID 67500944, compoundHCID 67502306HCID 67502306, compound

Product 1

HCID 131734927HCID 131734927, compoundYield 62%

Procedure

According to Example 1(6), a crude product of 4-{(3-ethyl-4-(quinolin-3-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl}-2-(1-methylpiperidin-4-ylamino)benzonitrile was prepared using compound (41h) instead of compound (1e) and using 4-amino-1-methylpiperidine instead of trans-aminocyclohexanol and was used in the subsequent reaction without being purified. According to Example 1(7), compound (71) (the second stage yield: 62%) was prepared as a white solid using 4-{3-ethyl-4-(quinolin-3-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl}-2-(1-methylpiperidin-4-ylamino)benzonitrile instead of compound (1f).

Workup

  1. customwas used in the subsequent reaction
  2. customwithout being purified
  3. customwas prepared as a white solid

Sources & evidence

ORD record
ord-9875a8596331471db4d163b6916c8fcc
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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