2-Amino-2-methyl-1-propanol → HCID 66779785, compound

HRID 1470343Notes

Reaction equation

HRID 1470343 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([C:14]2[O:22][C:21]3[C:16](=[N:17][CH:18]=[CH:19][C:20]=3[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:15]=2)=[CH:8][C:4]=1[C:5]([OH:7])=O.[NH2:29][C:30]([CH3:34])([CH3:33])[CH2:31][OH:32]>>[OH:32][CH2:31][C:30]([NH:29][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([C:14]2[O:22][C:21]3[C:16](=[N:17][CH:18]=[CH:19][C:20]=3[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:15]=2)[CH:10]=[C:11]([O:12][CH3:13])[C:3]=1[O:2][CH3:1])([CH3:34])[CH3:33]

Participants

3

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 66780323HCID 66780323, compound

Product 1

HCID 66779785HCID 66779785, compoundYield 28%

Procedure

Starting from 2,3-dimethoxy-5-(7-phenylfuro[3,2-b]pyridin-2-yl)benzoic acid (120 μmol) and 2-Amino-2-methylpropan-1-ol (123 μmol) the product is prepared analogously to “A43” and obtained as a yellow solid in a yield of 28%. HPLC (method A): Rt 2.64 min (purity 93.5%); LCMS (ESI+) (method E): Rt 1.9 min, M+H+ 447.2 m/z; 1H NMR (500 MHz, DMSO-d6) δ [ppm] 8.61 (d, J=5.2, 1H), 8.21 (s, 1H), 8.13-8.08 (m, 2H), 7.89 (d, J=2.1, 1H), 7.82 (s, 1H), 7.78 (d, J=2.1, 1H), 7.70-7.63 (m, 3H), 7.61-7.55 (m, 1H), 3.98 (s, 3H), 3.90 (s, br, 1H), 3.86 (s, 3H), 3.46 (s, 2H), 1.35 (s, 6H).

Workup

  1. customis prepared analogously to “A43”
  2. customobtained as a yellow solid in a yield of 28%

Sources & evidence

ORD record
ord-ecc48b375c1144e8951d90f488cf364a
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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