HCID 67501403, compound → HCID 178496770, compound

HRID 921531Notes

Reaction equation

HRID 921531 reaction equation
BrC1C=C(N2C3=NC=CC(C4C=C5C=CN(C[O:29]C)C5=NC=4)=C3C(C(C)C)=N2)C=CC=1C#N.[OH:34][C@H:35]1[CH2:40][CH2:39][C@H:38]([NH:41][C:42]2[CH:49]=[C:48]([N:50]3[C:54]4=[N:55][CH:56]=[CH:57][C:58]([C:59]5[CH:60]=[C:61]6[CH:67]=[CH:66][N:65]([CH2:68][O:69][CH3:70])[C:62]6=[N:63][CH:64]=5)=[C:53]4[C:52]([CH:71]([CH3:73])[CH3:72])=[N:51]3)[CH:47]=[CH:46][C:43]=2[C:44]#[N:45])[CH2:37][CH2:36]1>>[OH:34][C@H:35]1[CH2:40][CH2:39][C@H:38]([NH:41][C:42]2[CH:49]=[C:48]([N:50]3[C:54]4=[N:55][CH:56]=[CH:57][C:58]([C:59]5[CH:60]=[C:61]6[CH:67]=[CH:66][N:65]([CH2:68][O:69][CH3:70])[C:62]6=[N:63][CH:64]=5)=[C:53]4[C:52]([CH:71]([CH3:73])[CH3:72])=[N:51]3)[CH:47]=[CH:46][C:43]=2[C:44]([NH2:45])=[O:29])[CH2:37][CH2:36]1

Participants

3

Reactant 2

HCID 67501403HCID 67501403, compoundHCID 178496769HCID 178496769, compound

Product 1

HCID 178496770HCID 178496770, compoundYield 45%

Procedure

According to Example 1(6), a crude product of 2-(trans-4-hydroxycyclohexylamino)-4-{(3-isopropyl-4-(1-methoxymethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile was prepared using compound (15a) instead of compound (1e) and was used in the subsequent reaction without being purified. According to Example 1(7), compound (15) (the second stage yield: 45%) was prepared as a white solid using 2-(trans-4-hydroxycyclohexylamino)-4-{3-isopropyl-4-(1-methoxymethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}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-cd2bdd9103e74074a07554ff0643ff4d
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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