3-Isopropoxypropylamine → HCID 67501580, compound

HRID 921544Notes

Reaction equation

HRID 921544 reaction equation
BrC1C=C(N2C3=NC=CC(C4C=NC5C(C=4)=CC=CC=5)=C3C(C)=C2)C=CC=1C#N.C([O:33]CCCN)(C)C.[CH:38]([O:41][CH2:42][CH2:43][CH2:44][NH:45][C:46]1[CH:53]=[C:52]([N:54]2[C:58]3=[N:59][CH:60]=[CH:61][C:62]([C:63]4[CH:64]=[N:65][C:66]5[C:71]([CH:72]=4)=[CH:70][CH:69]=[CH:68][CH:67]=5)=[C:57]3[C:56]([CH3:73])=[CH:55]2)[CH:51]=[CH:50][C:47]=1[C:48]#[N:49])([CH3:40])[CH3:39]>>[CH:38]([O:41][CH2:42][CH2:43][CH2:44][NH:45][C:46]1[CH:53]=[C:52]([N:54]2[C:58]3=[N:59][CH:60]=[CH:61][C:62]([C:63]4[CH:64]=[N:65][C:66]5[C:71]([CH:72]=4)=[CH:70][CH:69]=[CH:68][CH:67]=5)=[C:57]3[C:56]([CH3:73])=[CH:55]2)[CH:51]=[CH:50][C:47]=1[C:48]([NH2:49])=[O:33])([CH3:39])[CH3:40]

Participants

4

Reactant 3

HCID 761943-IsopropoxypropylamineHCID 67500186HCID 67500186, compoundHCID 67501016HCID 67501016, compound

Product 1

HCID 67501580HCID 67501580, compoundYield 38%

Procedure

According to Example 1(6), a crude product of 2-(3-isopropoxypropylamino)-4-{(3-methyl-4-(quinolin-3-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl}benzonitrile was prepared using compound (40f) instead of compound (1e) and using 3-isopropoxypropylamine instead of trans-aminocyclohexanol and was used in the subsequent reaction without being purified. According to Example 1(7), compound (59) (the second stage yield: 38%) was prepared as a white solid using 2-(3-isopropoxypropylamino)-4-{3-methyl-4-(quinolin-3-yl)-1H-pyrrolo[2,3-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-5edc3dc9dcb14f1aa2147787c327a1c8
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

Loading…