(4-(4-BOC-piperazine-1-carbonyl)phenyl)boronic acid pinacol ester → HCID 67363617, compound

HRID 2046940Notes

Reaction equation

HRID 2046940 reaction equation
C1C2C(COC(=O)N[C@H](C([N:25]3[C:29]4=[N:30][CH:31]=[C:32](Br)[CH:33]=[C:28]4[C:27]([C@@H:35]([C:37]4[C:42]([Cl:43])=[CH:41][CH:40]=[C:39]([F:44])[C:38]=4[Cl:45])[CH3:36])=[CH:26]3)=O)CC(C)C)C3C(=CC=CC=3)C=2C=CC=1.C(OC([N:54]1[CH2:59][CH2:58][N:57]([C:60](=[O:76])[C:61]2[CH:66]=[CH:65][C:64](B3OC(C)(C)C(C)(C)O3)=[CH:63][CH:62]=2)[CH2:56][CH2:55]1)=O)(C)(C)C>>[Cl:45][C:38]1[C:39]([F:44])=[CH:40][CH:41]=[C:42]([Cl:43])[C:37]=1[C@H:35]([C:27]1[C:28]2[C:29](=[N:30][CH:31]=[C:32]([C:64]3[CH:63]=[CH:62][C:61]([C:60]([N:57]4[CH2:58][CH2:59][NH:54][CH2:55][CH2:56]4)=[O:76])=[CH:66][CH:65]=3)[CH:33]=2)[NH:25][CH:26]=1)[CH3:36]

Participants

3

Reactant 2

HCID 17749917(4-(4-BOC-piperazine-1-carbonyl)phenyl)boronic acid pinacol esterHCID 58431443HCID 58431443, compound

Product 1

HCID 67363617HCID 67363617, compound

Procedure

Example 69 was synthesized according to Suzuki coupling method described above for synthesis of example 66, using ((S)-1-{5-Bromo-3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]pyrrolo[2,3-b]pyridine-1-carbonyl}-3-methylbutyl)carbamic acid 9H-fluoren-9-ylmethyl ester and 4-[4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl ester. The crude material was purified by HPLC. MS (ES+): m/z=497.24, 499.25 (100, 69) [MH+]. HPLC: tR=0.72 min (HPLC-ACQUITY, Purity).

Workup

  1. customExample 69 was synthesized
  2. customdescribed above for synthesis of example 66
  3. customThe crude material was purified by HPLC

Sources & evidence

ORD record
ord-ec8ce877a2024d98bada151e98af5fe6
Source dataset
uspto-grants-2013_11
Patent number
US08592448B2

Reaction notes

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