HCID 201170, compound → HCID 6456223, compound

HRID 2085111Notes

Reaction equation

HRID 2085111 reaction equation
[K+].[Br-].CO[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[CH:13]1[C:25]2[NH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH2:16][CH2:15][NH:14]1.[CH3:26][O:27]C1C=C(C2C3NC4C(=CC=CC=4)C=3CCN2)C=CC=1OC.COC1C=C(OC)C=CC=1C1C2NC3C(=CC=CC=3)C=2CCN1>>[CH3:26][O:27][C:10]1[CH:5]=[C:6]([CH:13]2[C:25]3[NH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]=3[CH2:16][CH2:15][NH:14]2)[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=1

Participants

5

Reactant 4

HCID 201170HCID 201170, compound4×HCID 253877Potassium BromideHCID 3670531HCID 3670531, compound3×HCID 5210315HCID 5210315, compound

Product 1

HCID 6456223HCID 6456223, compound

Procedure

Pale yellow solid; C19H20N2O2; IR (KBr) v max 3420, 2910, 1605, 1465, 1350, 1305, 1155, 1065, 845, 785 cm−1; 1H-NMR (CDCl3) δ 5.03 (1H, s, H-1), 3.11(1H, m, H-3a), 3.35 (1H, m, H-3b), 2.91 (2H, m, H-4), 7.15 (3H, overlap, H-5,6,7), 7.56 (1H, d, J=7 Hz, H-8), 8.13 (1H, s, H-9), 6.47 (2H, d, J=2.1 Hz, H-2′,6′), 6.44 (1H, d, J=2.1 Hz, H-4′), 3.71 (6H, s, OMe); 13C-NMR (CDCl3) δ 58.3 (d, C-1), 43.0 (t, C-3), 22.3 (t, C-4), 109.8 (s, C-4a), 127.3 (s, C-4b), 121.6 (d, C-5), 119.2 (d, C-6), 118.1 (d, C-7), 110.8 (d, C-8), 144.1 (s, C-8a), 135.8 (s, C-9a), 134.2 (s, C-1′), 106.5 (d, C-2′,6′), 161.1 (s, C-3′,5′), 100.0 (d, C-4′), 55.3 (q, OMe); EIMS m/z 308 (100, M+), 307 (64), 279 (38), 278 (37), 264 (11), 249 (17), 248 (30), 233 (10), 220 (9), 217 (9), 204 (21), 191 (10), 171 (85), 154 (13), 144 (17), 130 (10), 115 (16), 102 (13), 95 (9), 77 (10).

Sources & evidence

ORD record
ord-5d0b1b6a6a4f46d4904db55bcfc708b0
Source dataset
uspto-grants-2004_04
Patent number
US06720331B2

Reaction notes

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