3-Amino-6-bromopicolinic acid → HCID 58464736, compound

HRID 1185288Notes

Reaction equation

HRID 1185288 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:22])[C:6]=1[O:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1.[NH2:23][C:24]1[C:25]([C:31](O)=[O:32])=[N:26][C:27]([Br:30])=[CH:28][CH:29]=1>>[NH2:23][C:24]1[C:25]([C:31]([NH:1][C:2]2[CH:3]=[N:4][N:5]([CH3:22])[C:6]=2[O:7][CH2:8][CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[O:32])=[N:26][C:27]([Br:30])=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 454804523-Amino-6-bromopicolinic acidHCID 58464811HCID 58464811, compound

Product 1

HCID 58464736HCID 58464736, compound

Procedure

Following the procedures for Example 141, tert-butyl 4-((4-amino-1-methyl-1H-pyrazol-5-yloxy)methyl)piperidine-1-carboxylate and 3-amino-6-bromopicolinic acid were reacted to give 3-amino-6-bromo-N-(1-methyl-5-(piperidin-4-ylmethoxy)-1H-pyrazol-4-yl)picolinamide, which was reacted with 2-fluorophenylboronic acid under palladium catalyzed Suzuki conditions to give 117 as a white solid (6.7 mg, 7.2%) over three steps. 1H NMR (400 MHz, DMSO) δ 9.66 (s, 1H), 8.10 (t, J=7.2, 1H), 7.71 (dt, J=37.9, 19.0, 1H), 7.60-7.25 (m, 5H), 7.03 (s, 2H), 3.97 (d, J=6.2, 2H), 3.72-3.42 (m, 3H), 2.76 (t, J=31.9, 2H), 2.36 (t, J=12.2, 2H), 1.88-1.53 (m, 3H), 1.25-0.99 (m, 2H). ESIMS m/z=425.1 (M+1)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-61382977462043489d8657c56c7cf238
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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