Hydrochloric Acid → HCID 117778825, compound

HRID 2206591Notes

Reaction equation

HRID 2206591 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5](=[O:10])[C:4]=1[CH2:11][NH:12][C:13]([C:15]1[C:23]2[C:18](=[N:19][C:20]([N:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)=[CH:21][CH:22]=2)[N:17]([CH:37]([CH3:41])[CH2:38][O:39][CH3:40])[C:16]=1[CH3:42])=[O:14].Cl>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5](=[O:10])[C:4]=1[CH2:11][NH:12][C:13]([C:15]1[C:23]2[C:18](=[N:19][C:20]([N:24]3[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]3)=[CH:21][CH:22]=2)[N:17]([CH:37]([CH3:41])[CH2:38][O:39][CH3:40])[C:16]=1[CH3:42])=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117779460HCID 117779460, compound

Product 1

HCID 117778825HCID 117778825, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To tert-butyl 4-(3-(((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-1-(1-methoxypropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-6-yl)piperazine-1-carboxylate (crude, used directly from last step). was added saturated hydrochloride solution in methanol (5 ml) at 0° C. The reaction mixture was allowed to room temperature and stirred for 2 hours. The reaction mixture was concentrated and purified by preparative HPLC (Mobile phase A: water with 0.05% ammonia solution; Mobile phase B: MeCN; column temperature: 30° C. Gradient: 30-60% B 10 min) to give a N-((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-(1-methoxypropan-2-yl)-2-methyl-6-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide (23 mg, 24.7%, two steps.). LRMS (M+1H) m/z: calcd 482.26. found 483. 1H NMR (400 MHz, CDCl3) δ: 1.59-1.62 (d, J=7.2 Hz, 3H), 2.21 (s, 3H), 2.71 (s, 3H), 2.96-3.01 (m, 4H), 3.23 (s, 3H), 3.40-3.43 (m, 4H), 3.81-3.88 (m, 4H), 4.10-4.14 (m, 1H), 4.61-4.63 (d, J=5.6 Hz, 2H), 5.91 (s, 1H), 6.41-6.44 (d, J=8.8 Hz, 1H), 7.41-7.45 (m, 1H), 7.90-7.93 (d, J=8.8 Hz, 1H).

Workup

  1. customwas allowed to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by preparative HPLC (Mobile phase A: water with 0.05% ammonia solution; Mobile phase B: MeCN; column temperature: 30° C. Gradient: 30-60% B 10 min)

Sources & evidence

ORD record
ord-a89202c910ce4cb581e39b38a7596ccd
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

Loading…